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Windham
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Vacation Rentals in Windham, NY
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Kid friendly (185)
Pet friendly (65)
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Mountain Views (14)
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Boat Available (4)
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5 km
Magic On Main
The Windham Path
Windham Mountain
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207 rentals
in Windham.
Cozy Caboose in the city
11 reviews
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres
9 reviews
Holiday Rental House
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9 bedrooms
5 bathrooms
Sleeps 30
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Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
9 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub
123 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Tuscan Year Round Beauty / Pickle Ball- Outdoor Kitchen
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 14
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FRESH SNOWSTORM Cutest Cabin in Windham for 2 People
45 reviews
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Windham Private heated indoor pool.
11 reviews
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 12
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'The Mountain House:' Windham Retreat w/ Hot Tub!
3 reviews
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Mountainview Lodge - Windham, Hunter Mountain
Holiday Rental House
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6 bedrooms
4 bathrooms
Sleeps 12
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Windham - Hot Tub�Game RoomFire Pit�Ski Views �
3 reviews
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 16
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TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6
7 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 7
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Luxury Log Cabin-Windham Mountain view, large lawn and deck, fire place, hot tub
6 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 12
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The Haüs Windham - Luxury 2 Bedroom Suite
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 8
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Redwood Retreat in Windham - minutes to the Mountain!
7 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Ski & Golf view farm house
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Blue Spruce Chalet — Hot Tub, Pet Friendly
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home
62 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 14
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Beautifully Restored 6BR in the heart of Windham
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 13
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Cozy Catskill Condo - 2 Mi to Windham Mountain Ski
4 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Black Dome - a 2B, 2B Condo 5 min from Windham, NY, and Windham Mt.
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Cozy Cabin Condo by the Mountain, 5mins to skiing!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Luxury Log Cabin in Windham, NY 4 br 4 ba Sleeps 10
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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GLASS MIRROR CABIN - HAUS WINDHAM
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Cozy Gateway Gem for 2 at Widham
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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1-Bedroom Luxury Suite + Full Kitchen + Dining - Haus Windham
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham
39 reviews
Cabin Holiday Rental
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1 bedroom
1 bathroom
Sleeps 2
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Rare Ski-In/Ski-Out Townhome! Windham Mountain at your back door!
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 12
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Peaceful Family Condo w/Deck + Mountain View!
2 reviews
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental
7 reviews
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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LUXURY DUPLEX SUITE WITH JACUZZI
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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LUXURY DUPLEX SUITE WITH JACUZZI
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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Sleeps
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Studio 3 BEDS-SLEEPS 3
6 reviews
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 3
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PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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Windham Mountain Ski House with Great Views
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous, First Class, 2 King apartment in downtown Windham
7 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Pebble Beach In Windham.
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Homey Windham Condo: Hike & Ski the Catskill Mtns!
2 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Clean Condo w/ Loft 2 Mi to Windham Mountain Ski!
8 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
Match:
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Cozy Mountain Condo
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 7
Match:
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Newly Built 1200sq ft Guest House 4min to Ski & Hiking
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Cozy Catskills Getaway w/ Yard & Mtn Views!
2 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Ski house in Windham near Hunter and Windham mountains
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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5 Minutes from Windham Mountain
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!
6 reviews
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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2 Bed Ski-In/Out Condo
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
The Haüs Windham - Luxury 2 Bedroom Suite w Loft
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Brand New A-Frame on West End of Main Street
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Windham Mountain Village Townhouse
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo
9 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 8
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Frequently Asked Questions about Windham
Do any vacation rentals in Windham have a pool?
Yes, here are some popular vacation rentals in Windham that have a pool:
WM Village walking distance to Windham Mt Hot Tub Pool 3b, 3Bath SKI
Cozy Caboose in the city
Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres
See all vacation rentals with a pool in Windham on Tripadvisor
Do any vacation rentals in Windham have internet access?
Yes, here are some popular vacation rentals in Windham that have internet access:
Cozy Caboose in the city
Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
See all vacation rentals in Windham on Tripadvisor
What are the best pet friendly rentals in Windham?
The best pet friendly rentals in Windham are:
Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
Mountainview Lodge - Windham, Hunter Mountain
See all pet friendly vacation rentals in Windham on Tripadvisor
What are some great rentals in Windham that are kid friendly?
Some of the most popular kid friendly rentals in Windham are:
Cozy Caboose in the city
Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
See all kid friendly vacation rentals in Windham on Tripadvisor