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Holiday Rentals in Bend

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    All 155 Rentals in Bend
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    Second Street Cottage-secluded downtown Bend, OR1 / 27
    (64)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Mt Bachelor Village -Top floor with 2 Queen beds +1 / 22
    (7)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    Updated 1BR Condo close to Mt. Bachelor1 / 14
    (4)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Three Rivers Retreat near Sunriver1 / 22
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Hot Tub
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2014
    We really enjoyed our stay. Great location right on the river. We had a blast with the kayaks and the jacuzzi. The fire pit was great. The beds were comfortable, cabin was well...
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    About this property
    Enjoy the comfort and serenity waiting for you at this peaceful home with views to the Big Deschutes River. Watch ducks stirring the water or a heron standing nearby. Listen to geese pierce the calm as you absorb the tranquil beauty of this natural setting. With easy access to Mt. Bachelor, come...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mt.Bachelor Village Resort--Comfortable living1 / 14
    (8)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2018
    If you want privacy and roominess close to skiing and just outside Bend, this the place. Some variation in the units but same basic amenities. Updates must be on a rotation...
    Reviewed 13 September 2017
    If you're looking for a quiet and out of the mainstream place, this is it!The surroundings are amazing.There are trails for walking and a short distance from water sports.I...
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    About this property
    Located on Bend's westside, a short walk along the Deschutes to the Old Mill district and off the Cascade lakes road to Mt.Bachelor, this cozy, recently upgraded condo in Mount Bachelor Village is a convenient base for any recreation or vacation plans. Features a full kitchen with stainless steel...
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    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tumalo Pines1 / 18
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Central Heating
    • Mountain Views
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 November 2016
    This house was beyond perfect for our 2 families (4 adults & 3 kids). It's remote but not too remote, and you feel instant serenity upon arrival. We had a blast wandering...
    Reviewed 12 March 2016
    We plan an annual trip with friends every year, spanning from the East Coast to the West Coast. I can honestly say that this was hands down the best spot we have stayed. If you...
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    About this property
    Private country setting with mountain views just 5 miles northwest of Bend. This 12 year old home sits on 20 acres of open juniper and pine forest, surrounded by other large, open tracks of land. The setting is lovely and private - like your own, private park with a house in the middle of it!...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bunk+Brew Historic Lucas House1 / 34
    (2)Excellent
    7 Bedrooms, 2 Bathrooms, Sleeps 28 Quick View
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    • Housekeeping Included
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    From the moment you walk in, Bunk + Brew lives up to its name! Whoever checks you in, Frankie or Jay, immediately gives you a tour of the wonderful historic building and offers...
    Reviewed 23 January 2017
    This place was awesome! The owners were super friendly and knowledgeable about activities to do in Bend. The house was cozy and clean. It was 1/4 mile from downtown and 35...
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    About this property
    The Bunk+Brew Historic Lucas House is the newest and ONLY affordable destination for the adventure traveler in downtown Bend, Oregon. 2.5 blocks from the Bend Ale Trail, the Lucas House (1910) is also Bend’s first and oldest brick building. Book a room (or bunk), grab a free check-in beer, and...
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    Bend, Central Oregon 97703
    Holiday Rental House - 7 Bedrooms, 2 Bathrooms, Sleeps 28
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    2BR Serene Sunriver Condo w/ Pool & Hot Tub - Minutes to The Village1 / 24
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2018
    This apartment provided a pleasant, low cost base for winter recreation in Sunriver. The mostly new floors, kitchen, and furnishings showed good taste and quality. The beds...
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    About this property
    PROPERTY OVERVIEW This 2BR condo offers a peaceful getaway with easy access to year-round activities. The welcoming first-floor unit features hardwood floors, new furnishings, and a private patio. On-site amenities include a seasonal heated pool and hot tub. Located less than one mile from...
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    Bend, Central Oregon 97707
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the beauty of Bend in this recently remodeled riverfront 2BR/2BA home. Enjoy idyllic views of the Deschutes River from the comfort of your outdoor hot tub and patio. Hold a movie night in the charming living room, with plush seating, a 43” flat screen TV, and polished hardwood floors...
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    Bend, Central Oregon 97703
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Porch
    • Grill
    • Parking
    • Mountain Views
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 3 bedroom 2 bath house, located right near the Old Mill district, is the perfect basecamp for your adventure in Central Oregon. You'll find comfort with 2 Queen beds, 1 California King, an open kitchen & living area, a garage and a fenced yard. Our home is great for kids and pets are...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury and Comfort at Mount Bachelor Village Condo, Views, Mountains and Lakes!1 / 42
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This is a great location to relax and escape the everyday hustle. It was great to have a big enough space to enjoy the family,cooking and playing together. The grand-kids loved...
    Reviewed 25 June 2017
    We were wowed by our initial first sight of the the condo and seeing the spectacular view of the mountains. The condo was newly renovated, immaculate, large and each bedroom...
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    About this property
    Located in beautiful Mount Bachelor Village offering spectacular views of downtown Bend & Old Mill District. This Condo House is 2.0 miles from downtown Bend and 20 miles from the slopes of Mount Bachelor Ski Resort. Nearby activities include downhill & cross-country skiing, ice skating,...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Widgi Elk Wonder This wonderful home combines the rustic appeal of lodge styling with modern amenities that will delight your guests—all in a location that puts you close to nature and convenient to the culinary and shopping delights of Bend. Located on the Widgi Creek Golf course, this spacious...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Terrace
    • Balcony
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The go-to destination for dining, shopping, and entertainment, the Old Mill District is within walking distance of this 3BR/2BA Bend house. A mix of old and new, the district offers boutique shops, art galleries, restaurants, amphitheater, and even a fly fishing course. When the weather’s warm, try...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Downtown Riverfront Cottage1 / 8
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Grill
    • Outdoor Dining Area
    • Waterfront
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2016
    My wife and I stayed at the Downtown Riverfront Cottage for a week and really enjoyed our time there. Great location to everything. Walking distance to downtown and the Old Mill...
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    About this property
    This house is right on the Deschutes River. You can walk one way to town (through Drake Park), and the other way also along the river to the Old Mill District. There really isn't a better location in Bend. One bedroom with queen bed and a really comfortable queen hide-a-bed. On the Deschutes...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    GREAT SW Bend location near Old Mill district 5 BR1 / 16
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Mountain Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2017
    The thing that pleased me the most was the leftover and staple food in the pantry and fridge. Thanks for being so fully stocked. I also borrowed a bicycle that was in the...
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    About this property
    This home is located on the desirable, southwest side of Bend in the heart of best recreation activities that Oregon has to offer. Easy access puts Mt. Bachelor skiing, fly fishing on remote lakes, mtn. biking, rafting, kayaking or the Old Mill District & Factory Outlet shopping, just minutes away....
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    Bend, Central Oregon 97201
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    'Scent of Pine, Sound of the Wind' Forested Remodeled Log Cabin Near Sunriver1 / 26
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2017
    This newly remodeled cabin worked perfectly for 3 adults and a dog and among the best places we have rented in our 20 years of vacation rentals. It is a little off the beaten...
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    About this property
    Classic log cabin charm meets industrial vintage style. Quality natural fibers and stone are used to update this space into a cozy log cabin experience you will soon not forget. Whether listening to the wind in the pine trees or enjoying a warm real log fireplace, the feel of the big city will be...
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    Bend, Central Oregon 97707
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7th Mountain Resort in Bend, Or1 / 21
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Children's Pool
    • Air Conditioning
    • Sauna
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Very comfortable lodging. The condo owner was very responsive to a small issue.The children enjoyed the pool and miniature golf.
    Reviewed 14 July 2016
    Checking in was our first Summer Time Delight. My friend loved the Iced Tea and shared one with me. And yes it was indeed the best ice tea we ever had. Made just right not too...
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    About this property
    Very clean, light and comfortable, well furnished one bedroom two full baths/shower/tub. Sleeps 4 very comfortably. Includes all utilities, wifi, basic cable, land line and use of all amenities. Fireplace ( presto log only), balcony with Deschutes Forest views and of the Paulina's. On site you...
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    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Stroll the River or downtown from this Condo- In the heart of Bend1 / 15
    (5)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Patio
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 February 2018
    This unit is a peaceful setting in the treetops next to the gorgeous Deschutes river park and an easy walk or bike ride to town. It is beautifully decorated and the bed and...
    Reviewed 11 November 2017
    Besides some issues w heat, this was a nice unit and very good communication with the owner! Nicely decorated and good layout. Within a mile of downtown, perfect. There was...
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    About this property
    This place has it all, super convenient and accessible to all of the amenities you want when you visit Bend. A stone's throw from the Deschutes River and it's miles of walking trails, a 5 minute walk to downtown, quick access to the Bend Parkway, and adjacent to restful Pioneer Park and of...
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    Location Information
    Bend, Central Oregon 97701
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll find the comforts of home at the Milwaukee Cottage, an updated vintage Bend cottage meticulously maintained and perfectly situated in Bend's popular westside. (updates to come November 1, 2017 new paint inside/out from ceilings to trim, all new furnishings/furniture including bedding,...
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    Bend, Central Oregon 97701
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Grill
    • Terrace
    • Patio
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a laid-back vacation in an idyllic countryside location at this 1BR/2BA condo in Bend. With a spot next to beautiful Pioneer Park on the banks of the Deschutes River, you can take scenic riverside strolls whenever the mood strikes. The condo is also within walking distance of downtown...
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    Bend, Central Oregon 97701
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Mountain Views
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The home is located in a quiet and peaceful setting, just minutes from all the great entertainment and restaurants to be found in downtown Bend. If you like great beer, you are in the right place. At last count, there were 31 micro breweries in town. Spring is a great time to be in the house....
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Washer
    • Terrace
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1BR/2BA Wall Street Condo accommodates up to four guests. Enjoy home-cooked meals from the full kitchen with sleek appliances and center island seating, or fire up the grill for an al fresco barbecue on either of the two private patios. Situated next to beautiful Pioneer Park, the condo...
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    Bend, Central Oregon 97701
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Patio
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    After a day of exploring scenic Bend, relax in the privacy of your own 1BR apartment, ideal for couples. Located on the second story of a larger home, the unit is spacious and comfortable, and has a private entrance. Spend your days exploring Bend’s state parks and the scenic Deschutes River....
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    Bend, Central Oregon 97703
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Classic Downtown Cottage1 / 30
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    This was a perfect house for our 2 families of 4. The four kids (cousins) stayed upstairs in the loft, and the 4 adults slept downstairs. The house was very clean and we...
    Reviewed 7 June 2016
    My family (me,wife,daughter,mother,sister,brother,brother's friend) all needed a place to stay for Memorial Day. We couldn't have found a better place. Big spacious rooms. Very...
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    About this property
    The Space This house is 2 bedrooms with a secluded loft. The master bedroom has a Queen sized bed, walk in closet, and a full sized bathroom. The second bedroom has a Queen sized bed and has access to the second bathroom. Both bathrooms have custom concrete counters and tiled walk in showers. The...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful SW Bend Home1 / 19
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2018
    We were in town with our kids for a couple of days, all of us from out of town. This house is very nice and clean, it's in a quiet neighborhood and close to downtown. If we had...
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    About this property
    Fantastic location in a quiet residential neighborhood, close to river trail access point, minutes from The Old Mill with lots of shopping and restaurants. An easy bike ride to the Deschutes River and downtown Bend. On site management available for anything you need during your stay, concierge...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Hot Tub
    • Terrace
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sasquatch Embrace the spirit of outdoor adventure in this beautiful Sunriver home with all the amenities you need for refreshing time away with family and friends. Nestled in pine woods, but bike ride to Sunriver Village and SHARC, this three-bedroom home may become your all-season favorite for...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Balcony
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful custom home with 5,000 square feet of living space features a gourmet kitchen, a game room, Jacuzzi tubs, and a well-appointed deck with a spectacular view of six Cascade peaks. This home offers four bedrooms (including two master suites), three full baths, two half-baths, and...
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    Location Information
    Bend, Central Oregon 97703
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    1st Street Rapids1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute and cozy cottage on the west side of Bend. A short stroll to First Street Rapids foot bridge and the river trail. 10 minute walk to downtown Bend with an assortment of restaurants, night life, and activities throughout the year. Convenient access to the parkway for the old mill or the...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two bedroom, one bath apartment above a horse barn in Alfalfa. Alfalfa is Centrally located between Bend, Redmond, and Prineville. We are 20 min East of Bend, 35 min South East of Redmond and same for Prineville. Apartment has beautiful views of the Cascade Mountains as you sit on back porch on...
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    Location Information
    Bend, Central Oregon 97701
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    In Downtown! Modern Home Comfort with Easy Access to Everything Bend! Hot tub1 / 26
    (16)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Easy access to everything in Bend. This home on The Bluffs in the Old Mill District is one block away from the bustling shops and restaurants, and is walking distance to the Les Schwab Amphitheater. Walk along the Deschutes River Trail that is only steps away. Or, just relax in the backyard and...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Skiing: Property Is In A Ski Resort
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    • Mountain Views
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    About this property
    Make the most of your mountain getaway when you stay at this 3-bedroom, 2-bathroom vacation rental house in Bend. Up to 7 guests can spread out in over 1,500 square feet of well-appointed living space. Breathe in the fresh air on the back deck as you take in the picturesque views of Pilot Butte....
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    A sunny one level home designed for comfort and location, location!!1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 9 August 2015
    We thoroughly enjoyed this stay in Bend and the accommodations were a big part of this enjoyment. It was close to everything in and around Bend and within 100 miles of many...
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    About this property
    Want a home that is close to it all -- this is your answer in fine form, the 'River Farewell'. The master bedroom is located on one side with an attached full bathroom. The other two bedrooms and guest bath are on the other side of the home. Located right in the middle is a delightful dining (6+)...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Portlandia Imagine having your own half-acre private nature reserve with a hot tub and visiting deer. Imagine that your home is in a quiet neighborhood. To top it off, you’re an easy, walkable mile to downtown Bend, and there’s a market, coffee shop and spa within two blocks. That’s the magic of...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tucked into a forested cul-de-sac this is a modern, 4 bedroom wooded delight!1 / 26
    (9)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Tall Timber is decorated to compliment where it sits amongst tall pines and a small herd of deer. Natures colors and tones have been embraced to create a sense of why you are here: the outdoors. Tall Timbers secluded shelter offers four bedrooms, a large dining area, a fireplace, and open living...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Light-filled 5BR, gameroom, hottub, ski, bike,golf1 / 31
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
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    About this property
    Our corner home sits on a tree-lined block within a family neighborhood with two private parks and walking paths. While Snow-capped peaks can be enjoyed from our windows, the home is conveniently located in town on the desirable Westside. It felt like home when we walked through the door of this...
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    Bend, Central Oregon 97701
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Bright Tree Court You’ll enjoy plenty of light and the pleasures of an immaculate, air-conditioned home when you book Bright Tree Court, which sits in a quiet neighborhood with easy access to Bend’s Westside. Extra comfy sofas surround a gas fireplace with a large flat screen TV in a great room...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    About this property
    Easy access to everything in Bend. This home on The Bluffs in the Old Mill District is one block away from the bustling shops and restaurants, and is walking distance to the Les Schwab Amphitheater. Walk along the Deschutes River Trail that is only steps away. Or, just relax in the backyard and...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Westside favorite with a hot tub - Perfect for skiing, biking and golf!1 / 17
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    The Trailhead sits in the perfect spot; positioned to view the Cascade Range, and walk your mountain bike across the street to Phil's Trail, thus the name of this awesome home! Century Drive is one half block from this home -- Get to Mt. Bachelor in 24 minutes, downtown and the Old Mill in four...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Balcony
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    About this property
    Walk to the river and Pioneer Park, or to the shops and restaurants downtown. This 1BR/2BA is convenient to all of Bend’s great amenities, and allows easy access to adventures farther afield. ABOUT THE CONDO The main living space gets lots of sunlight thanks to sliding glass doors leading to...
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    Bend, Central Oregon 97701
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Georgia Peach If your friends and family love Bend, why not station them two blocks from downtown in this beautiful shingled two-story? The quiet neighborhood and the private, fenced patio with barbecue, dining table and hot tub will make them forget they can step out the door and access...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The Whispering Pine Lodge near Sunriver, OR1 / 10
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 28 August 2017
    Our stay at Whispering Pine Lodge was one of the most peaceful and relaxing vacations we have had in a long time. The Cabin was beautiful and the location was quiet. We loved...
    Reviewed 10 January 2017
    Close to Sunriver, easily able to get where you want to go. Very comfortable and well kept. Would highly recommend!
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    About this property
    *FALL/WINTER/SPRING SPECIAL* Normally $150 a night now $125 a night. 4 night minimum. Not available with any other specials or Thanksgiving weekend or Christmas Break or Spring Break. Beautiful, built in 2006, 1800+ SqFt., Luxury 3 Bedroom lodge style vacation rental located 5 minutes from...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Parking
    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    This piece of country in town at the Old Mill has 2400 sq feet of upscale comfort in a quiet, peaceful, beautiful setting and great location. Bike to the Old Mill, hang out in the Tipi on the 1/4 acre yard, luxuriate in the comfort of this well appointed and spacious home. What more do you want?...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Blinn’s Landing Enjoyed and cherished by family and friends since 1951, this rustic log cabin, located at the confluence of Spring River and Deschutes River, adjacent to Sunriver Resort, offers a relaxing getaway with sparkling natural springs and picturesque mountain & river views. Book now and...
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    Bend, Central Oregon 97707
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Location and Comfort Make Portlandia a Favorite - Yes, the Hot Tub Helps!1 / 27
    (10)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Downtown and acreage, sounds amazing because it is. Perched at the base of Awbrey Butte sits the one level home called Portlandia. Mid-century furniture continues the open feel in this big home. The numerous windows flood light in the whole house. A spacious and modern four bedroom home, with a...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy incredible views of the Deschutes River during your stay at 'River Glen Retreat,' a 3-bedroom, 2.5-bathroom vacation rental house in Bend! The 2,500-square-foot home is located on the banks of the river and has large windows which provide guests with unbeatable vistas and also allow sunshine...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    As you drive towards your vacation rental on Wagon Master Way, you’ll immediately feel that this is not your ordinary Sunriver vacation. Located about 8 miles from the Village at Sunriver, you can count on being away from all of the hubbub of the busy village area, while still being able to soak up...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    About this property
    Vacation in luxury with all of your friends and loved ones when you book this gorgeous Sunriver lodge. There's plenty of room for everyone between the five bedrooms, not to mention spacious common areas and top-of-the-line amenities including a private hot tub, a private washer/dryer, and access to...
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    Bend, Central Oregon 97707
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    About this property
    Introduce your group to the luxury of this 5,000-square-foot home, situated on Fireglass Lake's edge. This home's private hot tub and access to resort amenities add magic to any family vacation, corporate retreat, or couples' trip. From the lower level's heated slate floors to the spacious patio...
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    Bend, Central Oregon 97707
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This waterfront 3BR/2.5BA home accommodates eight in a peaceful paradise beside the Deschutes River. Large picture windows overlook an expanse of pines and the rippling river, and the private backyard offers horseshoes, an outdoor dining area, and a fire pit. Bring your pole and your waders —...
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    Bend, Central Oregon 97703
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    River Farewell This charming one-story home is a wonderful haven for your stay in Bend. Its location across the street from Riverbed Park and the Deschutes River puts you within walking distance of many activities, from restaurants, shopping and even Les Schwab Amphitheater events! The park has a...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1
    Bend Holiday Rentals

    Surrounded by the stunning snowcapped peaks of the Cascade Mountains and the largest juniper forest in the western U.S., Bend is an outdoor recreation enthusiast’s paradise. Known for its cycling, hiking, kayaking, fishing and golfing, Bend, in the central part of the state, gets your adrenaline flowing in a variety of ways.

    Following a full day of intense activities, you’ll need a comfortable place to relax and recharge. Consider a spacious holiday rental where you can spread out and prepare your own meals rather than small hotel room. Whether you want to stay near downtown, in the Old Mill District, or near the Mt Bachelor ski resort, we have lots of villas, multi-bedroom homes, cabins, condos and other choices that are a better value than a hotel.

    Bend attractions and activities

    Bend is a phenomenal outdoor environment to leave the computers and televisions behind for a few hours or days. Family activities abound starting with the Lava Lands Visitors Center, about 15 minutes from downtown, where you’ll see the Lava Butte, a 7,000-year-old cinder cone lava formation that rises 500 feet. For thrill seekers, raft or kayak the white waters of the Deschutes River, take a panoramic chairlift ride up Mt. Bachelor, hike along Tumalo Creek or fish for trout at a well-stocked pond at Shevlin Park.

    Golfers have ten picturesque and challenging golf courses to play in the Bend area, including the Jack Nicklaus designed Pronghorn Golf Club, Crosswater at Sunriver Resort, a Bob Cupp design, and the affordable, family-owned Aspen Lakes Golf Club, where you’ll find lots of local residents.

    Downtown Bend is brimming with shops, galleries, restaurants, microbreweries and bars, which will enhance your visit to this former logging town.

    Holiday rentals for families

    From rustic cabins and cozy cottages to amenity-loaded condos and holiday homes with high-speed Internet, swimming pools, fireplaces and hot tubs, we can provide you with an extensive list of options in Bend. A great money-saving feature in all holiday rentals is the fully equipped kitchen, which allows you to provide delicious meals and snacks for your family instead of dining at pricey restaurants that’ll quickly destroy your budget.

    Deals on Bend holiday rentals

    When you visit Bend, your goal is to free your mind in the wondrous natural surroundings and the last thing you want to do is anguish about how much you paid for a cramped hotel room. Holiday rentals are a great value and we have special deals and discounts on a wide variety of properties in different areas of Bend in every price range.

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