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Holiday Rentals in Windham

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    All 27 Rentals in Windham
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    *4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Windham Mtn View1 / 24
    (31)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Mountain House Retreat-Catskill Mountains-Windham, NY:1 / 22
    (4)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Catskill Getaway apartment - Windham and Hunter Mountain Vacation Rental1 / 37
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Mountain Views
    • Patio
    • Washer
    • Balcony
    • Hot Tub
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape city stress when you retreat to ‘The Mountain House,’ a magnificent 4-bedroom, 2-bathroom Windham vacation rental house! Offering sleeping space for 10, modern amenities, a spacious deck with a hot tub and tranquil mountain views, this New York property is the secluded retreat you’ve been...
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    Windham, Catskill Region 12496
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom 2 Bath Quads Condominium - Condo located within minutes of Windham Ski Mountain, a short drive to Hunter Ski Mountain and between hiking and bike trails. Condo comfortably sleeps 7 and features a Fully-equipped eat-in kitchen. Fully equipped eat in kitchen seats 5, with coffee maker,...
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    Windham, Catskill Region 12496
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Country Convenient 2, 2bd townhouse Windham Hunter1 / 40
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Mountain Views
    • Terrace
    • Central Heating
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2018
    We were so impressed during our recent stay here; this townhouse is a 10-15 minute drive to Windham and was well-appointed, extremely clean and quiet, had plenty of room, and...
    Reviewed 20 June 2017
    Clean, comfortable and easily accessible. The condo has all you need and is well worth the price. We stayed for two nights during a festival at Hunter and were able to get...
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    About this property
    Spacious 2 bedroom apartment with queen size beds great for couples or a family with beautiful natural lighting located in scenic Prattsville, NY. Two levels. Downstairs: full kitchen, living room, flat screen TV, half bath (sink, toilet, washer/dryer). Upstairs: two bedrooms, each with a queen...
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    Windham, Catskill Region 12496
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Grill
    • Washer
    • Mountain Views
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful five bedroom home on three acres backing up to a stream. Four bedrooms on ground level and Master Bedroom on second floor with his and her bathrooms. Basement is newly refinished gameroom with brand new pool table, foosball, ping pong, card table, darts, and a bar. This house is ideal...
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    Windham, Catskill Region 12444
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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    ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***1 / 26
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Grill
    • DVD Player
    • Mountain Views
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2014
    We rented this house for the July 4th weekend and just loved it. The location is just perfect and very close to a lot of activities. The place is very comfortable and can easily...
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    About this property
    Available for weekends and short-term rentals during Spring, Summer, & Fall. ***Full season rental only in winter. $8500 from 12/1-4/1, not including utilities. $750 refundable damage deposit. One pet allowed.*** Charming and cozy 2 bedroom/2 bathroom house with gorgeous views of Windham Mountain...
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    Windham, Catskill Region 12496
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    The Catskills Tranquility House1 / 23
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Balcony
    • Central Heating
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Grill
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2017
    Went up here for a long weekend with family. Comfortable home and in good shape. Astonishing estate, I strongly recommend renting it.
    Reviewed 11 October 2016
    Everything was amazing! As soon as you drive up the driveway, you feel like you are in a different world. The house itself was truly spectacular along with the views! It...
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    About this property
    This property is located on 5 natural acres, in the majestic Catskill Mountains. The house itself is overlooking a 1 acre spring-fed pond. Kayak, fish, or swim out to the floating dock, or just relax on the deck overlooking the pond. Some of the amenities include: wood stove, barbecue, and...
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    Windham, Catskill Region 12496
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham1 / 34
    (34)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Porch
    • Mountain Views
    • Parking
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 December 2016
    Such a cute bungalow! Very cozy and well kept. Ella qas very kind and accommodating. I will definitely be back!
    Reviewed 16 November 2016
    If you are looking to explore the area, hiking, nature etc, sking, or like me, just looking for a cozy place to settle in for a quiet weekend and you don't need too much space...
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    About this property
    NO BOOKING FEE. CONTACT OWNER IF YOU'RE LOOKING FOR A BIGGER RENTAL OR IF DATES ARE BOOKED. Scroll down for rates and more info. Just Renovated! If you want to get away from everyday city noise, hear the birds, or just simply enjoy outdoors, we invite you to relax in our cute bungalow, Tiny House...
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    Windham, Catskill Region 12496
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Mountain Treasure  Cottage, WIndham, NY1 / 20
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Balcony
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2015
    We really enjoyed our brief stay over the Christmas break. Agnes was very accommodating by allowing us to have 7 people (as we had 3 kids). Its a cozy clean cottage and we had...
    Reviewed 1 September 2014
    Very pleased with my rental! Agnes was so wonderful with any questions I had and was very accommodating. She even suggested places to visit, which made my trip even better. The...
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    About this property
    Nestled on three acres of land with a panoramic view of the Catskill Mountain the Mountain Treasure Two-Bedroom Cottage is the ideal place to take in Mother Nature. Beautiful stream and an open space make this setting a truly magnificent place. This 2 level fully furnished cottage features a...
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    Windham, Catskill Region 12454
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Hot Tub
    • Washer
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in windham just 3- miles from town. Luxury home on 4-fenced acres overlooking the lake, farm meadow and the Thomas cole mountain range. 4-bdrms, 3-baths, 20' vaulted open living, dining and kitchen with fireplace. Finished lower level with billiard table, TV and bar. Ski room. Boulder...
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    Windham, Catskill Region 12496
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    WINDHAM MAGNIFICENT HOLIDAY GETAWAY1 / 54
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Patio
    • Washer
    • Housekeeping Included
    • Hot Tub
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2017
    Rented this house from Mike with a group of friends for Mountain Jam festival. The house has a ton of space and the backyard was perfect for an evening fire and BBQ.
    Reviewed 12 January 2017
    Me and the Fiance rented the house to usher in the New Year and I have to say I was floored by the amount of amenities / how well kept the house was ! View of the Mountain is...
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    About this property
    We are looking for families to treat this nice place like their own. Enjoy some quality time with family and friends!One of the loveliest homes in Windham not only for its quality and style but for its direct views of Windham Mt ski slopes. Views are so spectacular they'll take your breath away....
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    Windham, Catskill Region 12496
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 18
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    Beautiful apartment with great views!1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2016
    We rented this apartment for the 2015 ski season and could not have been happier! The unit is smartly laid out and beautifully furnished with a great kitchen! Easy access to...
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    About this property
    Beautifully decorated & spacious lower level apt in a new log home in Windham, NY. It comes fully equipped & is conveniently located near town, close to restaurants & bars, golf courses, a mountain bike park, walking & hiking trails, lakes for kayaking, tubing, & sailing, waterfalls, music...
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    Windham, Catskill Region 12496
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Grill
    • Secure Parking
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wake up to amazing views of Windham Mountain & enjoy the peace and quiet that surrounds you. The house sits on 15 beautiful acres. You will enjoy absolute privacy. You can explore on property. There is a private pond where you can fish. Also tons of nearby activities which include hiking, fishing,...
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    Windham, Catskill Region 12496
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Mountain House. Sitting on five beautiful acres with views of 4 of the highest peaks in the Catskills, this is the perfect family getaway spot for all seasons. Ask about All-Inclusive Packages, which can include, on-site concierge, car and chef services and much more! In the winter...
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    Windham, Catskill Region 12496
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 22
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    Country Convenient - cozy 2bd apartment in Windham1 / 17
    (4)Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Mountain Views
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2015
    I was happy to find the apartment on the Internet, after searching for accommodations to attend a family wedding. First, the price was great!. Second, Ella answered all my...
    Reviewed 27 March 2015
    The cozy apartment was just that. Everything was very clean and warm and inviting. The kitchen is just right. We could either eat in or dine out within easy walking distance...
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    About this property
    Cozy, two bedroom apartment, ideal for couples or family. Beds: 1 queen, two singles. Stones throw from Ski Windham, 7 miles to Hunter Mountain. Located in Hensonville (part of Windham, NY) Walking distance to grocery, diner, 4 star restaurant, bar and lounge. Off street parking. BBQ area and...
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    Windham, Catskill Region 12439
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2015 Ski Season rental available. Located 5 minutes from Windham Mountain Ski Resort. The apartment features 2 bedrooms, one bath, furnished with quaint country antiques, and new furniture. Spotlessly clean, convent. The kitchen is fully equiped with dishes, utensils, pots, and pans, microwave,...
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    Windham, Catskill Region 12496
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great views of Windham Mountain and the valley left and right. The house is 1.3 miles from Ski Windham. Large living room/dinning area with birds eye view of mountain and valley from a wraparound deck. Enjoy an adult cocktail watching the New Years Fire works or the stars. BBQ grill on the deck....
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    Windham, Catskill Region 12496
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain1 / 43
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Parking
    • Mountain Views
    • Porch
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2016
    A very nice and quiet cottage for a romantic get away if you like the mountains. Place was very clean and kept up. Ella was great in preparing the place for us as we requested...
    Reviewed 7 January 2016
    Ella ,whom we contacted for this rental , responded very promptly. It was a last minute arrangement on our part and we could not have done it without Ellla's prompt and...
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    About this property
    NO BOOKING FEE. CONTACT US IF CALENDAR SHOWS BOOKED. Scroll down for rates and more info. We also offer other vacation rentals. Get away from everyday city noise and enjoy the outdoors and the beautiful Catskill Mountains region! Breathe in the fresh mountain air. If you're looking for a Catskills...
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    Windham, Catskill Region 12496
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Central Heating
    • Wi-Fi
    • Terrace
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This amazing 4 bedroom apartment is located at Crystal Pond Condos in Windham near the ski resort on Windham Mountain. you can rent for Thanksgiving till end of March including the new year and Christmas. Free transportation is provided from the condo to the ski resort on Windham. best for every...
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    Windham, Catskill Region 12439
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The chic, laid-back beauty and authentic comfort of our farm, house & gardens, will inspire you! Enjoy the soothing, peaceful and relaxing rural countryside. Just 25 min. driving to Albany and 35 min. to Hudson. - THE HOUSE .- Originally built in the mid to late 19th Century, the farmhouse was...
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    Windham, Catskill Region 12193
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • DVD Player
    • Parking
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable, two-story, 7-room family home on an acre of land. Recently redecorated, new carpeting, new appliances. Master bedroom has king-size bed, 2nd and 3rd bedrooms each have a twin bed. Living Room, separate Dining Room, Kitchen, and Playroom. Full Bath. Front and back porches. Ample...
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    Windham, Catskill Region 12454
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    The Presidential Suite at Brie & Bordeaux1 / 9
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 October 2015
    Beautiful guesthouse tucked away in Windham, NY. Great view of the mountain from the living and dining room. Guesthouse has full working kitchen, large Presidential Suite with...
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    About this property
    An upscale and contemporary suite located in the heart of the Catskills, above Bistro Brie & Bordeaux, on Main Street, in Windham, NY. Create you getaway weekends, weeks and season stays. The suite has a king bed, queen bed, and one bunk bed. The great room, incorporates the living room with flat...
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    Windham, Catskill Region 12496
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a cozy 3 bedroom Cape Cod with open loft and skylights. Less than 1 mile to Hunter Mountain! Great for Festivals! Wooded end of road location with Apple Trees during season. Stone wood-burning fireplace in living room, deck for outdoor dining in the front of the house with a large back...
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    Windham, Catskill Region 12450
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Central Heating
    • Parking
    • Patio
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large beautiful home on 6 acres of land only a couple minutes to Ski Windham Mountain and snow tubing park. Large outdoor fire-pit surrounded by huge rocks with Adirondack chairs. Nice outdoor hot tub. Out side cooking grill and outside deck looking at Ski Windham Mountain. Home has 5 bedrooms...
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    Windham, Catskill Region 12496
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Grill
    • Washer
    • Patio
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is 2 miles to Windham and 7.9 miles to Hunter Mountains, 1 mile from busy Main Street full of stores and restaurants. It is a welcoming place located on the main road on 1.6 acres of landscaped property with great views all around. The house is fully equipped for gracious living and...
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    Location Information
    Windham, Catskill Region 12496
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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