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Vacation Rentals in Windham, NY

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    Travellers to Windham are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 23
    5 of 5 stars (15) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is...
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    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,... View all property information
    Location Information
    Windham, Catskill Region 12496
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Central Heating
    • Wi-Fi
    • Terrace
    • Parking
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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... View all property information
    Location Information
    Windham, Catskill Region 12439
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    • Patio
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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.... View all property information
    Location Information
    Windham, Catskill Region 12496
    1 / 35
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Parking
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
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    About this property
    Please scroll down for RATES (NO BOOKING FEE IS ADDED WHEN YOU BOOK THIS PROPERTY, SAVING YOU ~15% Booking Fee). Contact owner if you're looking for a larger vacation rental unit or a cabin. Cozy, 1 bedroom apartment, ideal for a couple. 3rd person requests considered on case to case basis. Beds:... View all property information
    Location Information
    Windham, Catskill Region 12439
    5 of 5 stars Reviewed 5 weeks ago
    I really enjoyed this place and highly recommend it. The rooms were colorful, nicely decorated and up-to-date. All the basics were provided including a small fridge with the...
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    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Among the nicest properties in Windham. Lovely large home nestled quietly on 12 usable acres with bucolic bridle paths joined to hiking trails. A true feel of Tuscany on the property beginnging at the front door. An all-season beauty. Pick wild Chanterelles / Porcini / Ramps and Blackberries in... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 Bedrooms, 3 Bathrooms, Sleeps 15 | Quick View
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    • Patio
    • Hot Tub
    • Satellite TV
    • Grill
    • Washer
    • Mountain Views
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
    • Smoking allowed
    • Elder access
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    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... View all property information
    Location Information
    Windham, Catskill Region 12444
    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
    • Grill
    • DVD Player
    • Mountain Views
    • Secure Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    Charming and cozy 2 bedroom/2 bathroom house with gorgeous views of Windham Mountain and the best of both worlds--a 1.5 mile drive to the mountain (10 miles to Hunter) and less than a minute drive to town (10-15 min walk). Situated on a little less than 2 acres of land on Route 23, but set back... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 of 5 stars 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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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Washer
    • Outdoor Dining Area
    • Air Conditioning
    • Mountain Views
    • Parking
    • Internet Access
    • Satellite TV
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Available for rent by owner is a 4 bedroom, 2 bathroom, four season country home which is about a mile from Windham mountain, and 8 miles to Hunter Mountain in the Catskill Mountains. You will find this house clean and charming, and it is especially family friendly. It is situated on a spur road... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 of 5 stars Reviewed 24 June 2014
    The house was close to good resteraunts and small shops. Very close to Ski Slopes and Hiking trails. Also some good fishing not far away. Super Market was a trip, so stop on...
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
    • Mountain Views
    • Hot Tub
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Cuomo’s Cove is located in the Majestic Catskill Mountains in Windham, N.Y. We offer 1-3 bedroom luxury suites for nightly and weekly rental. Our completely furnished suites offer the style, comfort and conveniences found only in your own home – Plus amenities such as: private hot tubs, Jacuzzi... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 of 5 stars Reviewed 7 September 2014
    We wanted to get away for a few relaxing days after our wedding and we found the perfect place for a peaceful, tranquil and lovely getaway @ Cuomo's Cove. Our accomodations were...
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Mountain Views
    • Wi-Fi
    • Secure Parking
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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... View all property information
    Location Information
    Windham, Catskill Region 12496
    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Garden
    • DVD Player
    • Parking
    • Patio
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
    • Smoking allowed
    • Elder access
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    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... View all property information
    Location Information
    Windham, Catskill Region 12454
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Satellite TV
    • Washer
    • Grill
    • DVD Player
    • Mountain Views
    • Central Heating
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    The house has 3 bedrooms, each equipped with quality queen beds, and 2 baths. Additionally, each room has personalized electric heat, on top of central heating provided for the whole house. Kitchen is fully equipped with all necessary appliances (fridge, stove, oven, dishwasher, coffee maker,... View all property information
    Location Information
    Windham, Catskill Region 12413
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Washer
    • Parking
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
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    • x
    About this property
    Beautiful, fully equipped and furnished home within 10 minutes to the town of Windham. The area is a four season destination with a variety of recreational activities, and cultural events. The country setting and view from the deck are both peaceful and relaxing. Wake up to amazing sunrises and... View all property information
    Location Information
    Windham, Catskill Region 12407
    5 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Mountain Views
    • Patio
    • Grill
    • Washer
    • DVD Player
    • Balcony
    • Hot Tub
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    The Eagle View Ranch, a New York Catskill Estate is one of the most splendiferous of them all and uniquely built by a world traveler and outdoor enthusiast. This family owned estate encompasses unbeatable hiking and walking, snowshoeing and cross-country skiing, and canoeing and kayaking. Located... View all property information
    Location Information
    Windham, Catskill Region 12492
    1 / 9
    5 of 5 stars (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
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 of 5 stars Reviewed 27 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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    1 / 8
    4.5 of 5 stars (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Washer
    • Porch
    • Internet Access
    • Grill
    • Patio
    • Satellite TV
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    4 bedroom chalet (upper apartment, duplex,) with 2 baths. Traditional ski chalet ready for this ski season. Very clean 4 bedrooms, two full bath, Windham Ski House. 6 beds in 4 bedrooms, 2 couches. Great for young ski families. Two bedrooms and full bath on main level and two bedrooms and bath on... View all property information
    Location Information
    Windham, Catskill Region 12439
    5 of 5 stars Reviewed 27 December 2013
    We contacted the owner at the very last minute and she luckily had a cancellation. We arrived to find an immaculately clean incredibly well stocked home! We couldn't have enjoyed...
    4 of 5 stars Reviewed 30 October 2013
    Owner went above and beyond to make our stay perfect. The house was so well stocked. The beds were comfortable and the house was pefect and cozy for our large family. The hot tub...
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    1 / 25
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
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    • Mountain Views
    • Outdoor Dining Area
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
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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... View all property information
    Location Information
    Windham, Catskill Region 12439
    5 of 5 stars Reviewed 8 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...
    5 of 5 stars 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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    1 / 21
    5 of 5 stars (31) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Internet Access
    • Grill
    • Air Conditioning
    • Porch
    • Mountain Views
    • Parking
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Please scroll down for RATES. (NO BOOKING FEE IS ADDED WHEN YOU BOOK THIS PROPERTY, SAVING YOU 5-15% Booking Fee) 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 bungalow. Surround yourself with nature and breathe in... View all property information
    Location Information
    Windham, Catskill Region 12496
    4 of 5 stars Reviewed 25 September 2015
    When we first arrived ,I was a little takin back by the size of the cottage. I turned out to be perfect . Everything was clean . Ella , the owner was quick in returning our text...
    5 of 5 stars Reviewed 31 July 2015
    this cozy little place was perfect for our weekend getaway. the bungalow was a great balance of local charm, character and complete amenities, as was the town of prattsville. as...
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    1 / 26
    5 of 5 stars (21) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Washer
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    WELCOME HOME TO YOUR OASIS AWAY FROM IT ALL! Le Chalet Montreuil is set up as a TRUE SECOND HOME FURNISHED with all that you need and want for the entire length of your stay. There is no reason to ever leave the COMFORTS & CONVENIENCES of the chalet, if you so desired to stay on the property with... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 of 5 stars Reviewed 1 October 2015
    Angel was a very interactive host who made every effort to make sure we had everything we needed. He provided a wealth of information on the rental and activities in the...
    5 of 5 stars Reviewed 16 September 2015
    My husband and I rented this home with our two small children and another couple, and it was perfect. The owner, Angel, is a pleasure to work with. She responds to every e-mail...
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    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Satellite TV
    • Internet Access
    • Parking
    • DVD Player
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Two-story townhouse overlooking Windham Mountain less than 2 miles away. Large open floor plan consisting of a fully equipped kitchen and beautifully furnished living room & dining room. Includes 2 bathrooms and 2 bedrooms + a small sleeping loft and a den sleeping 6 adults. The home has a lovely... View all property information
    Location Information
    Windham, Catskill Region 12496