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Holiday Rentals in Windham

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    ₹ 21,878 Average
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    ₹ 0₹ 64,000+
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    Travellers to Windham are booking October dates now. Secure your holiday home today, and have the perfect trip.
    All 26 Rentals in Windham
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    *4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Windham Mtn View1 / 24
    (28)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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    The Catskills Tranquility House1 / 23
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • DVD Player
    • Mountain Views
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We had a lovely time - a get away from the city life. The owner was very helpful and easy to deal with.
    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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    Catskill Getaway apartment - Windham and Hunter Mountain Vacation Rental1 / 37
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Parking
    • Air Conditioning
    • Mountain Views
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2017
    We enjoyed this pleasant, well maintained and clean space with just enough kitchen equipment for simple cooking. The only thing renters should be aware of, that a close look at...
    Reviewed 24 August 2016
    My wife and I had a wonderful weekend at the cabin, and Ella, the owner, was very friendly and helpful at answering our questions. Hensonville, though small, has several nice...
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    About this property
    NO BOOKING FEE. CONTACT OWNER IF LOOKING FOR LARGER VACATION RENTAL OR IF the CALENDAR IS BOOKED. We rent other vacation rentals in the Catskills. Scroll down for rates and more info. Cozy, 1 bedroom apartment, ideal for a couple. 3rd person requests considered on case to case basis. Beds: 1...
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    Windham, Catskill Region 12439
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Mountain Treasure  Cottage, WIndham, NY1 / 15
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Terrace
    • Parking
    • 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.<BR>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
    • 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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    Country Convenient 2, 2bd townhouse Windham Hunter1 / 40
    (2)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 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...
    Reviewed 14 June 2016
    We rented this brand new condo to take care of overflow on our family reunion. The place is perfect, brand new, nicely decorated and easy to find and use. The town is nice and...
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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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    Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham1 / 40
    (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
    • 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. 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 Vacation Rental....
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    Windham, Catskill Region 12496
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • 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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    Location Information
    Windham, Catskill Region 12496
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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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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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Mountain Views
    • Porch
    • 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. See CatskillBungalow. 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...
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    Location Information
    Windham, Catskill Region 12496
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Patio
    • Hot Tub
    • 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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    Country Convenient - cozy 2bd apartment in Windham1 / 17
    (4)Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    WINDHAM MAGNIFICENT HOLIDAY GETAWAY1 / 54
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 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 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Mountain Views
    • Wi-Fi
    • Secure Parking
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Fall Getaway!!! Call or email now for last minute tour of Catskills reservation!! This home is a super immaculate, upscale, classic ski chalet nestled on 1 private wooded acre. Home features 3 bedrooms and 2 full baths and comfortably sleeps 4 adults and 4 children. Den with wood burning...
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    Windham, Catskill Region 12496
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Parking
    • Washer
    • DVD Player
    Suitability
    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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    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
    • 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, 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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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • 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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    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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    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    • Skiing: Property Is In A Ski Resort
    • 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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Parking
    • 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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    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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    Beautiful apartment with great views!1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Balcony
    • Washer
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Mountain Views
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous Windham Mountain home with spectacular views (sleeps up to 14). Celebrate Thanksgiving, Christmas (through 12/29) and other weekends/weeks in November and December (2 night minimum). Ski in/ski out-snow permitting.But regardless, blissful, idyllic relaxation guaranteed. Thanksgiving week...
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    Location Information
    Windham, Catskill Region 12496
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • 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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    Location Information
    Windham, Catskill Region 12496
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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