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Holiday Rentals and Homes in Windham, NY

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    Travellers to Windham are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    5 Bedrooms, 3 Bathrooms, Sleeps 15 | Quick View
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    5 of 5 stars (23) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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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 / 37
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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 and manage 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.... View all property information
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    Windham, Catskill Region 12439
    5 of 5 stars Reviewed 22 February 2016
    This little suite (bath/kitchenette next to bedroom) is terrifc for a couple's getaway in our opinion. Walk right out your private entrance to excellent restaurants - or venture 3...
    5 of 5 stars Reviewed 7 January 2016
    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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    5 of 5 stars (32) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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 bungalow. Surround yourself with nature... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 of 5 stars Reviewed 8 June 2016
    I'm a doctoral student and I've been trying to finish writing my dissertation but there are always distractions, so I decided to rent this cabin for a week for a little R&R and...
    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...
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    1 / 13
    5 of 5 stars (2) Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    The Mountain House Retreat is situated on 7 beautiful acres in the Catskill mountains with panoramic views, a private fresh water pond and lovely forest landscape. This fully furnished mountain house, has an open living space with fireplace. 5 bedrooms, 2 baths, internet service, 2 outdoor decks... View all property information
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    Windham, Catskill Region 12496
    1 / 23
    5 of 5 stars (15) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    NO BOOKING FEE. CONTACT US IF CALENDAR SHOWS BOOKED. Scroll down for rates and more info. We own and manage 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... View all property information
    Location Information
    Windham, Catskill Region 12496
    4 of 5 stars Reviewed 6 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 efficient...
    5 of 5 stars Reviewed 12 August 2015
    Exactly what two busy people who spend a lot of time around people needed after doing a Warrior Dash race. We live only 2.5 hours away but we were able to just sit back and relax...
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    4.5 of 5 stars (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    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
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    Windham, Catskill Region 12439
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
    Location Information
    Windham, Catskill Region 12450
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
    Location Information
    Windham, Catskill Region 12496
    8 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
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    • Satellite TV
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    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... View all property information
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    Windham, Catskill Region 12496
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Child-friendly
    • x
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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
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    Windham, Catskill Region 12496
    1 / 25
    3.5 of 5 stars (3) Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Christiansen House is located in the Northern Catskill Mountains of upstate New York. A charming destination year round, the Christiansen House features 3 bedrooms, 3 bathrooms, a fully equipped kitchen, dinning room, open living area with fireplace, over 1700+ sq. ft. in all. Enjoy the... View all property information
    Location Information
    Windham, Catskill Region 12424
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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
    5 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    • Air Conditioning
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    • x
    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
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Terrace
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    • x
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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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    About this property
    2 bedroom, 2 bathroom Mountain view condo two miles from Windham Mountain Four Season cozy two bedroom condo sleeps 4 adults and 2 young children comfortably with two bedrooms, 2 full bathrooms, fully equipped kitchen, living room with wood burning fireplace and private deck. Two miles from... View all property information
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    Windham, Catskill Region 12496
    1 / 9
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
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    • Pet-friendly
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    • x
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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... 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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    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
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    • x
    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 / 20
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • Private Garden
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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... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 of 5 stars 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 all...
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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. Short drive to Ski Windham and Hunter Mountain. Nearby is a local grocery store, liquor store, laundry mat and florist in the Prattsville Plaza. Food &... View all property information
    Location Information
    Windham, Catskill Region 12496
    5 of 5 stars Reviewed 13 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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    The Pinnacle Condominiums are the newest and closest lodging at Hunter Mountain. Conveniently perched on top of Hunter Mountain base Lodge these 7 units offer easy access to all amenities, 5 dining choices and an easy walk to town. The ultimate for ski on ski off, tubing, dining, festivals,... View all property information
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    Windham, Catskill Region 12442
    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
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    Windham, Catskill Region 12496
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • Pet-friendly
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    • Smoking allowed
    • x
    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... View all property information
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    Windham, Catskill Region 12193
    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • x
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    • x
    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
    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • x
    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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    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Satellite TV
    • Internet Access
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    • Washer
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    • Child-friendly
    • x
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    • Smoking allowed
    • 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