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Holiday Rentals in Winter Park

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    ₹ 10,608 Average
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    ₹ 0₹ 65,000+
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    Travellers to Winter Park are booking July dates now. Secure your holiday home today, and have the perfect trip.
    All 386 Rentals in Winter Park
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    Ski In/Out Resort Village #4283 - Free Activities/No Deposit/Resort Discounts1 / 24
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Ski In/Out Resort Village #3302 - Free Activities/No Deposit/Resort Discounts1 / 24
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Remodeled Winter Park Condo - Sleeps 61 / 22
    (82)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ski In/Out Resort Village #3324 - Free Activities/No Deposit/Resort Discounts1 / 24
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • Hot Tub
    • Satellite TV
    • Central Heating
    • Sauna
    • Housekeeping Included
    • Wi-Fi
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 2017
    We loved the proximity of this unit to the slopes. This was a guys trip and we had plenty of room to spread out with there being 3 different rooms in this unit. Very clean and...
    Reviewed 22 February 2017
    Fraser crossing is conveniently located in the Village, a very short walk to the slopes, resturants and shops. This condo is perfect for up to 3 couples or a large group of...
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 bedroom/2 bath condo sleeps...
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    Ski In/Out Resort Village #4546 - Free Activities/No Deposit/Resort Discounts1 / 24
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Sauna
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Hot Tub
    • Shared Indoor Pool
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2017
    This was a nice condo at a nice price in an excellent location! The best spot we've stayed so far in Winter Park.
    Reviewed 23 March 2017
    We have visited Winter Park many times. This was our first time lodging at the base. It was great and worth the price. The Founders Pointe condo was great. The hot tub was...
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 1 bedroom/1 bath condo sleeps...
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Ski In/Out Resort Village #4370 - Free Activities/No Deposit/Resort Discounts1 / 24
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Housekeeping Included
    • Shared Indoor Pool
    • Wi-Fi
    • Satellite TV
    • Sauna
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2017
    Mud season was just the right time for two people who don't ski. We love nature and enjoyed hiking on the trails even with the mud.
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 1 bedroom/1 bath condo sleeps...
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located near the town of Winter Park, Colorado, this premier vacation rental home is bright and beautiful! Hardwood floors throughout and upscale furnishings provide a sumptuous environment for your get-a-way! The gourmet kitchen has tile counter tops and new appliances, allowing you to whip up...
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    Winter Park, Grand County 80482
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy, Family-Friendly, End Unit1 / 17
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Central Heating
    • Shared Indoor Pool
    • Internet Access
    • Satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2017
    My family and I had a great vacation and the condo was a perfect place to rest after a long day of skiing. Literally right next to the amazing rec center with three hot tubs...
    Reviewed 21 September 2016
    We enjoyed our weekend in Winter Park w/ our 5 & 2 year old girls. The place is well furnished and comfortable, and our girls loved the brand new adjacent rec center with...
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    About this property
    2 bedroom, 1.25 bathroom, quiet, top floor end unit. Great for families looking for affordability and easy access to amenities. Front-loading washer and dryer in unit. Next to clubhouse with pool, hot tubs and a rec center. Sledding hill, playground, restaurants and bakery all within walking...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 B/7.5 BA Winter Park Amazing views, Reunions1 / 38
    (3)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2014
    We stayed at Oso's Overlook for our wedding weekend in June. The views are absolutely breathtaking, and the house is immaculate. Our guests walked in and were blown away with...
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    About this property
    Our 6,000 sq foot mountain home, located on a high point just above Fraser, boasts the most spectacular distance views in the Winter Park area! Through three walls of windows you'll see Beyer's Peak, the slopes of Winter Park, the Devil's Thumb, and the Indian Peaks all around while you look down...
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    Location Information
    Winter Park, Grand County 80442
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    Ski In/Out Resort Village #3133 - Free Activities/No Deposit/Resort Discounts1 / 24
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Sauna
    • Shared Indoor Pool
    • Mountain Views
    • Satellite TV
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We loved our stay in this unit with our dog, and found this area to be very pet friendly. I appreciated Logan's great communication leading up to our stay. The condo was very...
    Reviewed 24 April 2017
    The unit was very clean and accessible. The unit is conveniently located on the first floor. It's furnished with the basics, the decor is simple but tasteful. We would highly...
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 bedroom/2 bath condo sleeps...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Founders Pointe 44471 / 23
    (2)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2015
    This was the third year we stayed in this condo. We kept returning because we love Winter Park and the condo was great for the first two years - clean, good condition...
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    About this property
    This newly built, contemporary vacation rental property is located near The Village of Winter Park Resort, right at the base of the Winter Park mountain. This condo is in great proximity to the Zephyr Express and Discovery Park for your learn to ski winter vacation or the abundance of activities...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Braidwood Unit 3041 / 18
    (10)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The check in process was quick and easy, my observation is that they do not offer a late check out option. The unit was in a good location just off the main street in Winter...
    Reviewed 3 April 2013
    Our stay in Winter Park was very enjoyable! The condo was unexpectedly nicer than we had imagined it would be.. Rustic and comfortable with all the amenities we could ever...
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    About this property
    The Braidwood Condominiums are a popular choice for those requiring in-town, comfortable accommodations at a very affordable price. The Main Street of downtown Winter Park is one block from the property so there is nothing that you cannot easily access from shopping, restaurants, winter activities...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Charming Log Cabin w/Hot Tub, Deck, Ping Pong,Wifi1 / 30
    (10)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Patio
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 2016
    Cabin was nice, perfect for two, we had a minor issue with the shower door but is was corrected the same day.The only thing that bothered me was having to walk down the stairs...
    Reviewed 20 July 2016
    My family and I stayed at Bear Claw Cabin and had a great time! The deck out back was my favorite as it was perfect for an afternoon reading in the sun. The teenagers loved...
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    About this property
    This fully equipped log cabin in the town of Winter Park sleeps 6 and is right on the shuttle route. (Shuttle stops at end of driveway.) It offers a cozy cabin feel yet is spacious and super comfortable. Two bedrooms - one with queen bed the other with a double plus bunk bed. Gas fireplace, WiFi,...
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    Winter Park, Grand County 80482
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Hideaway Village Ladora 31 / 10
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Terrace
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The open floor plan on the main level has the living room with comfortable mountain themed furnishings, flat screen TV, VCR, DVD, free in unit Wi-Fi access, wood burning fireplace and queen sofa sleeper. A total of 930 square feet of living space is in town home with the dining area being open to...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Iron Horse Resort 30941 / 34
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Parking, pool, bedrooms and living area were all good. The bathrooms did not have grab bars, but otherwise all was good.
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    About this property
    2 bedroom vacation condo at the Iron Horse Resort, just steps from the Winter Park ski area. This unit provides a gas fireplace, full kitchen and a private balcony. The master bedroom offers a queen bed and a full bath with separate vanity area. The additional bedroom has 2 twin beds. There is a...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Winter Park 4BR w/Hot Tub On Free Shuttle Route1 / 26
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • Parking
    • Washer
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2017
    Booked this cabin for a week of skiing at Winter Park Resort. It was close to the slopes and close to town so the location is perfect. Inside it is decorated very nicely with...
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    About this property
    Welcome to Alpine Hollow! Experience the Colorado Rocky Mountains like never before from this warm and inviting home, well-situated for the many year-round activities Winter Park has to offer! With 4 bedrooms, 3 bathrooms, and 2 living areas spread over 3 levels, it comfortably accommodates up to...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Base Camp 4721 / 29
    (23)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2016
    ABSOLUTELY WONDERFUL! Great location, outstanding amenities, loved waking up to hearing the running waterfall outside the condo! There were 40 of us that came to Winter Park...
    Reviewed 26 July 2012
    What a great vacation rental. After the beautiful 2 hour drive to Winter park from Denver, we couldn'thave been happier! This is a wonderful place! From the large gorgeous...
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    About this property
    In this stunning, inviting and airy retreat you can find yourself completely at ease. The open floor plan and cathedral ceilings showcase magnificent high-end finishes throughout the home. The large wraparound porch houses a hot tub, a great place to soak and enjoy the view and sounds of Jane...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
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    Elk Lodge1 / 31
    (32)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 19 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With high-end finishes throughout the home, including granite countertops and vaulted ceilings, Elk Lodge is the epitome of luxury and comfort. Dine al fresco on the large porch with a sizeable gas grill, or cozy up in front of the fireplace with hot cocoa. Enjoy a private hot tub and a full...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 19
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    Ski In/Out Resort Village #3129 - Free Activities/No Deposit/Resort Discounts1 / 24
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • Housekeeping Included
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Sauna
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2017
    Stayed 5 days for a ski vacation. Condo was clean and comfortable plus really close to lifts. Reasonable price too.
    Reviewed 20 March 2017
    The condo is on the first floor of the building with easy access to the parking garage and ski locker and front of the condo. It was clean and well equipped. Would stay here...
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 bedroom/2 bath condo sleeps...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Fresh In-town condo w/W&D, pool, spa, hi-tech toys1 / 22
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Sauna
    • Satellite TV
    • Hot Tub
    • Internet Access
    • DVD Player
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 January 2017
    The condo was great. Within walking distance to town. The owners were very responsive to our questions. I would highly recommend you stay at this condo. I will be booking it again!
    Reviewed 9 September 2016
    We went up for a three day mini vacation. It was so nice that we will be going back soon.The hot tub and pool were wonderful and very clean. The condo was outstanding. Every...
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    About this property
    A memorable and fun Winter Park vacation is assured when you stay at this beautiful and newly transformed 2 bedroom, 2 bathroom mountain home at Beaver Village Condominiums. Under new ownership, this home has been extensively remodeled just in time for your ski vacation! Improvements include: •...
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Base Camp 4801 / 29
    (24)Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2016
    We enjoyed a week in this home during the July 4th celebration in Winter Park. There was plenty of room for all the adults and kids. It was close to many activities and places...
    Reviewed 25 April 2016
    We were invited to stay with extended family who had rented Basecamp 480 for a ski vacation. We happen to live within an hour and a half of Winter Park, so it was a nice chance...
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    About this property
    With plenty of seating for large gatherings, this open floor plan is the perfect place for conversation and comfort. Every detail is in place to indulge your senses: a chef's kitchen for producing gourmet delights, two living areas for unwinding and socializing. Lots of natural light highlights the...
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    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Colorado condo vacation rental is a lovely decorated 2 bedroom condo with 899 square feet of living space has a private balcony accessible from the living room with forest views and one block from Main Street in downtown Winter Park. The main living area has a tiled floor throughout, wood...
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom Colorado vacation rental condo has 1, 200 square feet and is on the 3rd floor of the building with a modern decor, 3 bedrooms and 2 bathrooms and is a great family condo rental. Please also note that Building 19 does not permit smoking outside within 20 feet of the building, in...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sawmill Station 2201 / 31
    (5)Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the peaceful atmosphere of Sawmill Station, whilst being only a short stroll from all the conveniences of town, in this gorgeous three-story townhome. This end-unit is in excellent condition with new furnishings and authentic Colorado art & décor, and offers plenty of room for families &...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Base Village Loft 1011 / 33
    (21)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An exquisite place to host large family getaways, this ski-in/ski-out property is the only 4-bedroom condo right at the Winter Park base. The space features two distinctive and comfortable living areas with plenty of room to spread out. This exclusive property is located right in the heart of...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious home easily accommodates several families with plenty of private sleeping room, and large, relaxing gathering areas.This space features a private hot tub, deluxe comfortable furniture, and a spacious great room with fireplace and large flat screen TV for gathering after a fun filled...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    Vasquez Retreat1 / 32
    (18)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Internet Access
    • Mountain Views
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2016
    Another great weekend at Vasquez Retreat, this was our third stay at this fabulous home and it has not lost it's appeal. From the spacious Master bedroom with it's gorgeous view...
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    About this property
    Vaulted ceilings over picture windows with incredible views, a full kitchen, large dining area and a separate breakfast bar, plus tons of places to sleep or relax- just a few of the many perks of this beautiful Vasquez Retreat home. With comfortable leather furniture and impressive mountain décor,...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    Base Camp 4921 / 30
    (9)Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the heart of Base Camp, this luxury townhome exudes relaxation and high-end touches. Earlybirds can enjoy the sunrise over the forest from the east-facing deck, or the kitchen-adjacent opposite deck offers a soothing place to enjoy a soak in the hot tub. Multiple fireplaces throughout...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The luxury and comfort of this upscale property is shown in the rooms which are equipped with the latest appliances and electronics. A tri-level floor plan, all units are non-smoking, have 2 decks, private outdoor hot tubs, heated garages, gas fireplaces and washers/dryers. A 3 bedroom 4 bathrooms...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Snowshoe House1 / 21
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious and authentic cabin exudes a special personality from the moment you enter and offer guests a spectacular mountain view from the private deck and main living room. The Snowshoe house is located within the Hideaway Village town home complex at the top of the hill and is also on the...
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    Location Information
    Winter Park, Grand County 80482
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bear Crossing 14151 / 23
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • Mountain Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 December 2014
    We were 3 families with kids and the town home was excellent for us. Very clean - There are 3 bedrooms and extra bunk beds where we let the kids hangout and play. Its very close...
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    About this property
    Enjoy beautiful, high end mountain furnishings and amenities when you stay at this three level townhome overlooking Downtown Winter Park.  Large picture windows light up the main living area and open up spectacular views of the valley and mountains all along the Continental Divide. Inside, you'll...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Ski In/Out Resort Village #4474 - Free Activities/No Deposit/Resort Discounts1 / 24
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Sauna
    • Satellite TV
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We have had a lovely stay in this lovely 2bedroom with patron condo. Would definitely return and might have to permanently move here!
    Reviewed 12 February 2017
    Location was great, unit was very clean. We used the pay garage underneath the building, which I would recommend since there is not a load/unload area otherwise. The unit has...
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 bedroom/2 bath condo sleeps...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Winter Park Place #16! Beautiful, elegant 2br/2bth1 / 23
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Patio
    • Washer
    • Central Heating
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2016
    The condo is beautiful, spacious, and relaxing. The pictures look great but it is still so much better in person. Kitchen and bathrooms are fresh, and functional. The shower and...
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    About this property
    This is a super cozy and elegant 2 bedroom/2 bathroom, over 1200 square foot condo with everything you need right at your finger tips, conveniently located 1/3 of a mile from Winter Park Resort. The living room is a place where you can relax and "melt," with a warm fireplace, open kitchen, dining...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ALL INCLUSIVE(NO EXTRA CLEANING FEES) FOR SKI SEASON BOOKINGS for 4+ NIGHTS!!!!!!! *CALENDAR IS ACCURATE* - 4 NIGHT MINIMUM - (2-3 nights accepted if only avail. Costs vary.) CALL FOR VALUE OPTIONS! * FREE BUS SERVICE FROM OUR NEIGHBORHOOD TO THE WINTER PARK BASE- WKENDS + HOLIDAYS...(PENDING...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Hideaway Village Alpine 41 / 10
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A lovely townhome with 880 square feet of living space on two interior floors, this 2 bedroom unit is a good family rental. The main floor has a comfortable open living room with TV, VCR, wood burning fireplace and queen sofa sleeper and has access to the small private patio. Adjacent to the...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Winter Park's most convenient in town lodging is Crestview Place, located adjacent to restaurants, bars and the shopping complex of Cooper Creek Square. This spacious and updated unit has 2 bedrooms with loft and 2.75 bathrooms on the 5th floor of the building with a total of 1, 344 square feet of...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    New Riverfront - Ground Level condo!1 / 43
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Sauna
    • Waterfront
    • Mountain Views
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2017
    We recently spent a weekend in Winter Park with our 3 young children. The condo looked amazing in the pictures, and even better in person! Everything in the condo was upgraded...
    Reviewed 5 October 2015
    The condo was lovely and very comfortable. We enjoyed listening to the river flowing over the rocks sitting on the patio. The fresh cut flowers that greeted us on our arrive was...
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    About this property
    Completely remodeled RIVERFRONT SUITE with high end custom finishes! At the base of Winter Park Ski Resort! This ground level condo is located in Winter Park Place, a small private complex nestled in the trees and backing to the beautiful Fraser River in Old Town Winter Park!. Right by the Fraser...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This ground floor 3 bedroom, Hi Country Haus family unit has a spacious 1, 023 square feet, on the second floor, but an end unit that overlooks the Fraser River in the summer months. In the living room a flat screen TV is mounted next to the wood burning fireplace and has additional entertainment...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Base Village Loft 1091 / 25
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relish luxurious living in this one-level loft, located right in the Village at Winter Park, for an experience you won't soon forget. This spacious loft boasts an array of impressive amenities that will surely impress.  Enjoy granite countertops, high-end furnishings and appliances, and a private...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Base Camp 4941 / 30
    (11)Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2015
    This house was very nice and spacious! It is three different levels, so be prepared to climb some stairs. The rooms are spaced apart that noise levels of kids weren't a...
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    About this property
    With a unique layout and high-end finishes, including granite countertops, expertly crafted woodwork, and two wet bars, this mountain escape is the epitome of relaxation. Tall windows with incredible mountain views, and beautiful decor give this place an air of luxury. This expansive space includes...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    Base Camp 4761 / 25
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Absolutely great place for our college friends ski trip. Keyless Entry is a must on every future trip I book! We will be back to this place in the future years.The only...
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    About this property
    Relax and completely ignore the outside world with this incredible view of Jane Creek and the tranquil forest behind it. Tall ceilings, multiple lounge areas and open floor plan enhance this home's spacious and comfortable feel.  The expansive kitchen has exquisite counters, a large island for...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sophisticated Old Town loft has a deliciously hip, and urban vibe throughout. Situated just off of Winter Park Drive in Old Town, this high-end home offers convenient access to Winter Park Resort (just 1/3 mile away), while enjoying a quiet location in an exclusive two-residence building.  The...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Slopeside 2041 / 24
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2016
    This condo is wonderful! Beautiful layout with plenty of space for our family. Our favorite place was the kitchen and great room. We love to cook and there was plenty of space...
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    About this property
    Ascend into a piece of paradise in this beckoning mountain home nestled amongst the trees. You will relax in quiet warmth with views of the peaks; yet a mere one stop away on the free resort shuttle, is the bustle of activity at Winter Park Village. After a day of activity and laughter, your group...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This downtown Winter Park modern 3 bedroom condo has been recently updated 3 bedroom unit has 759 square feet on the third floor of the building - a great family vacation rental. The interior décor has a modern theme with newer furnishings and is an end corner unit for additional peace and quiet....
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Mimi's Cabin1 / 18
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Terrace
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Washer
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2016
    Great cabin, beautiful view, great little town. Loved it. Beautiful inside the cabin as well! Rooms were up to date, well cleaned, good lay out. We slept 9 comfortably.
    Reviewed 17 January 2016
    This place offered a great amount of space for our 5 teenagers, four adults to spend time together as well as have our own areas to have some privacy. Beautiful surroundings to...
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    About this property
    Sitting atop Forest Trail, this charming, authentic cabin exudes warmth and character from the moment you enter. Mimis Cabin is on the free shuttle route where the buses literally stop outside the front door providing transportation to the Ski Area, 3 miles away or you can take the bus the 2/3 mile...
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    Location Information
    Winter Park, Grand County 80482
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Huge, Luxury Townhome in Town - Hot Tub!1 / 13
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Satellite TV
    • Central Heating
    • Grill
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location, Location For your next winter ski vacation or summer getaway, stay at our luxurious 4 bedroom / 4.5 bath townhouse in the heart of Winter Park. This is the one spot you will come back to over and over again! The convenience is unbeatable ...walk to restaurants, bars,...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Hi Country Haus Unit 19131 / 24
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 3rd floor vacation condo rental has 899 square feet of living space and is comfortably decorated. ***Please also note that Building 19 does not permit outside smoking within 20 feet of the building, no smoking within the condo units and no pets are allowed. The main living room area offers a...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mary Jane's Dream Home1 / 34
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the HGTV 2007 Dream Home!  Tucked away in the secluded Bridger's Cache neighborhood below the Mary Jane slopes, this luxurious yet delightfully welcoming home has all the trappings you would expect of its coveted title.  Enjoy classic mountain architecture with a contemporary twist, plus...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This rare Base Village Loft boasts a unique floor plan all on one level! This beautiful space sits perched directly above the Village walk and is just steps away from dining, nightlife, outdoor activities, and a few minutes walk to the Zephyr lift. Beautiful wood and stone accents highlight the...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 11
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    Hi Country Haus Unit 7051 / 23
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 2 bedroom 1 bathroom unit has been recently renovated and has 651 square feet of living space. In the living room, a flat screen HDTV is mounted next to the wood burning fireplace, VCR, DVD, free in unit Wi-Fi access with a queen sofa sleeper make this area a nice relaxing getaway. The kitchen...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Previous
    Winter Park Holiday Rentals

    Looking for family ski fun, or golf and mountain biking within 90 minutes of Denver? Year-round, a money-saving Winter Park holiday rental is your quickest road from Denver to Rocky Mountain recreational fun. Don’t want to drive the 90 minutes from the Denver airport to your money-saving Winter Park holiday rental? The old Rio Grande Scenic Railroad Company weekend ski train may be out of operation. But you can still kickback and enjoy the Rocky Mountain scenery from the comfort of Amtrak’s California Zephyr. Allow at least 2 hours for the daily rail journey between Denver Union Station and Fraser-Winter Park station.

    Railroad Starts Winter Park

    The railroad started it all. Winter Park came into existence way back when the railroad constructed the Rocky Mountains/Moffat Tunnel and workers needed places to live in this rugged mountain wilderness. The City of Denver launched Winter Park as a ski resort in 1940 by constructing a ski tow at West Portal. Today there are 25 lifts servicing 143 designated ski trails on about 3,000 acres, of which over a third is off-piste terrain. And money-saving holiday rental homes, apartments, townhouses, and condos make Winter Park a comfortable year-round family resort.

    Winter Fun

    Winter Park usually kicks off skiing before Thanksgiving, as there are 26 trails and about 300 acres for the snowmaking machines. As the snow accumulates and winter season gets into full swing, your money-saving holiday rental also becomes your portal to glade skiing, cross-country skiing, snow cycling, snowboarding, snowshoeing, Snowcat tours and NASTAR racing. Guided touring opportunities abound for the whole family to learn about the native Rocky Mountain plants and animals. For holiday DVDs and training purposes, the Ski and Ride School rents helmet cams to capture the mogul runs and downhill action.

    Summer Fun

    Golf at Grand Elk, Headwaters, or one of the 9-hole courses up the highway near Granby. From Granby, it is a short drive to Rocky Mountain National Park. The kids will enjoy rounds of mountainside mini-golf and the Alpine Slide. Meanwhile fly fish the Fraser River. Wade in or take a boat to fish the Colorado River, while the kids practice clowning and juggling at Winter Park Circus Camp. Mountain bike, rollerblade or picnic along the five-mile Fraser River Trail. Checkout Trestle Bike Park, which has hosted Mountain States Cup cross country racing, slalom, downhill, and super D.

    More Winter Park Fun

    The whole family will enjoy the Old West post office and stage stop at Cozens' Ranch House Museum. Cowboy sing-a-long campfires and mountain man storytelling will leave the kids spellbound. Learn astronomy at the two-hour Star Safaris produced by the University of Colorado's Fiske Planetarium. Then relax at your money-saving Winter Park holiday rental, before your next adventure.

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