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Holiday Rentals in Windham

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
203 rentals in Windham.
Cozy Caboose in the city, holiday rental in Windham
Cozy Caboose in the city, holiday rental in Windham
Cozy Caboose in the city, holiday rental in Windham

Cozy Caboose in the city

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres, holiday rental in Windham
Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres, holiday rental in Windham
Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres, holiday rental in Windham

Ultimate Windham Mountain Farm Retreat: Spectacular 9 Bedroom Home on 30 Acres

Holiday Rental House
9 bedrooms
5 bathrooms
Sleeps 30
Match: Sleeps
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Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!, holiday rental in Windham
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!, holiday rental in Windham
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!, holiday rental in Windham

Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, holiday rental in Windham
Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, holiday rental in Windham
Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, holiday rental in Windham

Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tuscan Year Round Beauty / Pickle Ball- Outdoor Kitchen, holiday rental in Windham
Tuscan Year Round Beauty / Pickle Ball- Outdoor Kitchen, holiday rental in Windham
Tuscan Year Round Beauty / Pickle Ball- Outdoor Kitchen, holiday rental in Windham

Tuscan Year Round Beauty / Pickle Ball- Outdoor Kitchen

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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FRESH SNOWSTORM Cutest Cabin in Windham for 2 People, holiday rental in Windham
FRESH SNOWSTORM Cutest Cabin in Windham for 2 People, holiday rental in Windham
FRESH SNOWSTORM Cutest Cabin in Windham for 2 People, holiday rental in Windham

FRESH SNOWSTORM Cutest Cabin in Windham for 2 People

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Windham Private heated indoor pool., holiday rental in Windham
Windham Private heated indoor pool., holiday rental in Windham
Windham Private heated indoor pool., holiday rental in Windham

Windham Private heated indoor pool.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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'The Mountain House:' Windham Retreat w/ Hot Tub!, holiday rental in Windham
'The Mountain House:' Windham Retreat w/ Hot Tub!, holiday rental in Windham
'The Mountain House:' Windham Retreat w/ Hot Tub!, holiday rental in Windham

'The Mountain House:' Windham Retreat w/ Hot Tub!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mountainview Lodge - Windham, Hunter Mountain, holiday rental in Windham
Mountainview Lodge - Windham, Hunter Mountain, holiday rental in Windham
Mountainview Lodge - Windham, Hunter Mountain, holiday rental in Windham

Mountainview Lodge - Windham, Hunter Mountain

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Windham - Hot Tub�Game RoomFire Pit�Ski Views �, holiday rental in Windham
Windham - Hot Tub�Game RoomFire Pit�Ski Views �, holiday rental in Windham
Windham - Hot Tub�Game RoomFire Pit�Ski Views �, holiday rental in Windham

Windham - Hot Tub�Game RoomFire Pit�Ski Views �

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps  6, holiday rental in Windham
TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps  6, holiday rental in Windham
TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps  6, holiday rental in Windham

TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Luxury Log Cabin-Windham Mountain view, large lawn and deck, fire place, hot tub, holiday rental in Windham
Luxury Log Cabin-Windham Mountain view, large lawn and deck, fire place, hot tub, holiday rental in Windham
Luxury Log Cabin-Windham Mountain view, large lawn and deck, fire place, hot tub, holiday rental in Windham

Luxury Log Cabin-Windham Mountain view, large lawn and deck, fire place, hot tub

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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The Haüs Windham - Luxury 2 Bedroom Suite, holiday rental in Windham
The Haüs Windham - Luxury 2 Bedroom Suite, holiday rental in Windham
The Haüs Windham - Luxury 2 Bedroom Suite, holiday rental in Windham

The Haüs Windham - Luxury 2 Bedroom Suite

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Redwood Retreat in Windham - minutes to the Mountain!, holiday rental in Windham
Redwood Retreat in Windham - minutes to the Mountain!, holiday rental in Windham
Redwood Retreat in Windham - minutes to the Mountain!, holiday rental in Windham

Redwood Retreat in Windham - minutes to the Mountain!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski & Golf view farm house, holiday rental in Windham
Ski & Golf view farm house, holiday rental in Windham
Ski & Golf view farm house, holiday rental in Windham

Ski & Golf view farm house

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Blue Spruce Chalet — Hot Tub, Pet Friendly, holiday rental in Windham
Blue Spruce Chalet — Hot Tub, Pet Friendly, holiday rental in Windham
Blue Spruce Chalet — Hot Tub, Pet Friendly, holiday rental in Windham

Blue Spruce Chalet — Hot Tub, Pet Friendly

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home, holiday rental in Windham
The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home, holiday rental in Windham
The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home, holiday rental in Windham

The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Beautifully Restored 6BR in the heart of Windham, holiday rental in Windham
Beautifully Restored 6BR in the heart of Windham, holiday rental in Windham
Beautifully Restored 6BR in the heart of Windham, holiday rental in Windham

Beautifully Restored 6BR in the heart of Windham

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Cozy Catskill Condo - 2 Mi to Windham Mountain Ski, holiday rental in Windham
Cozy Catskill Condo - 2 Mi to Windham Mountain Ski, holiday rental in Windham
Cozy Catskill Condo - 2 Mi to Windham Mountain Ski, holiday rental in Windham

Cozy Catskill Condo - 2 Mi to Windham Mountain Ski

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Black Dome - a 2B, 2B Condo 5 min from Windham, NY, and Windham Mt., holiday rental in Windham
Black Dome - a 2B, 2B Condo 5 min from Windham, NY, and Windham Mt., holiday rental in Windham
Black Dome - a 2B, 2B Condo 5 min from Windham, NY, and Windham Mt., holiday rental in Windham

Black Dome - a 2B, 2B Condo 5 min from Windham, NY, and Windham Mt.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Cabin Condo by the Mountain, 5mins to skiing!, holiday rental in Windham
Cozy Cabin Condo by the Mountain, 5mins to skiing!, holiday rental in Windham
Cozy Cabin Condo by the Mountain, 5mins to skiing!, holiday rental in Windham

Cozy Cabin Condo by the Mountain, 5mins to skiing!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!, holiday rental in Windham
Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!, holiday rental in Windham
Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!, holiday rental in Windham

Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Log Cabin in Windham, NY 4 br 4 ba Sleeps 10, holiday rental in Windham
Luxury Log Cabin in Windham, NY 4 br 4 ba Sleeps 10, holiday rental in Windham
Luxury Log Cabin in Windham, NY 4 br 4 ba Sleeps 10, holiday rental in Windham

Luxury Log Cabin in Windham, NY 4 br 4 ba Sleeps 10

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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GLASS MIRROR CABIN - HAUS WINDHAM, holiday rental in Windham
GLASS MIRROR CABIN - HAUS WINDHAM, holiday rental in Windham
GLASS MIRROR CABIN - HAUS WINDHAM, holiday rental in Windham

GLASS MIRROR CABIN - HAUS WINDHAM

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Gateway Gem for 2 at Widham, holiday rental in Windham
Cozy Gateway Gem for 2 at Widham, holiday rental in Windham
Cozy Gateway Gem for 2 at Widham, holiday rental in Windham

Cozy Gateway Gem for 2 at Widham

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1-Bedroom Luxury Suite + Full Kitch - Haus Windham, holiday rental in Windham
1-Bedroom Luxury Suite + Full Kitch - Haus Windham, holiday rental in Windham
1-Bedroom Luxury Suite + Full Kitch - Haus Windham, holiday rental in Windham

1-Bedroom Luxury Suite + Full Kitch - Haus Windham

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1-Bedroom Luxury Suite + Full Kitchen + Dining - Haus Windham, holiday rental in Windham
1-Bedroom Luxury Suite + Full Kitchen + Dining - Haus Windham, holiday rental in Windham
1-Bedroom Luxury Suite + Full Kitchen + Dining - Haus Windham, holiday rental in Windham

1-Bedroom Luxury Suite + Full Kitchen + Dining - Haus Windham

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham, holiday rental in Windham
Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham, holiday rental in Windham
Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham, holiday rental in Windham

Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham

Cabin Holiday Rental
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rare Ski-In/Ski-Out Townhome! Windham Mountain at your back door!, holiday rental in Windham
Rare Ski-In/Ski-Out Townhome! Windham Mountain at your back door!, holiday rental in Windham
Rare Ski-In/Ski-Out Townhome! Windham Mountain at your back door!, holiday rental in Windham

Rare Ski-In/Ski-Out Townhome! Windham Mountain at your back door!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Peaceful Family Condo w/Deck + Mountain View!, holiday rental in Windham
Peaceful Family Condo w/Deck + Mountain View!, holiday rental in Windham
Peaceful Family Condo w/Deck + Mountain View!, holiday rental in Windham

Peaceful Family Condo w/Deck + Mountain View!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental , holiday rental in Windham
Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental , holiday rental in Windham
Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental , holiday rental in Windham

Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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LUXURY DUPLEX SUITE WITH JACUZZI, holiday rental in Windham
LUXURY DUPLEX SUITE WITH JACUZZI, holiday rental in Windham
LUXURY DUPLEX SUITE WITH JACUZZI, holiday rental in Windham

LUXURY DUPLEX SUITE WITH JACUZZI

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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LUXURY DUPLEX SUITE WITH JACUZZI, holiday rental in Windham
LUXURY DUPLEX SUITE WITH JACUZZI, holiday rental in Windham
LUXURY DUPLEX SUITE WITH JACUZZI, holiday rental in Windham

LUXURY DUPLEX SUITE WITH JACUZZI

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Studio 3 BEDS-SLEEPS 3, holiday rental in Windham
Studio 3 BEDS-SLEEPS 3, holiday rental in Windham
Studio 3 BEDS-SLEEPS 3, holiday rental in Windham

Studio 3 BEDS-SLEEPS 3

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY, holiday rental in Windham
PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY, holiday rental in Windham
PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY, holiday rental in Windham

PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Windham Mountain Ski House with Great Views, holiday rental in Windham
Windham Mountain Ski House with Great Views, holiday rental in Windham
Windham Mountain Ski House with Great Views, holiday rental in Windham

Windham Mountain Ski House with Great Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous, First Class, 2 King apartment in downtown Windham, holiday rental in Windham
Gorgeous, First Class, 2 King apartment in downtown Windham, holiday rental in Windham
Gorgeous, First Class, 2 King apartment in downtown Windham, holiday rental in Windham

Gorgeous, First Class, 2 King apartment in downtown Windham

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Homey Windham Condo: Hike & Ski the Catskill Mtns!, holiday rental in Windham
Homey Windham Condo: Hike & Ski the Catskill Mtns!, holiday rental in Windham
Homey Windham Condo: Hike & Ski the Catskill Mtns!, holiday rental in Windham

Homey Windham Condo: Hike & Ski the Catskill Mtns!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Clean Condo w/ Loft 2 Mi to Windham Mountain Ski!, holiday rental in Windham
Clean Condo w/ Loft 2 Mi to Windham Mountain Ski!, holiday rental in Windham
Clean Condo w/ Loft 2 Mi to Windham Mountain Ski!, holiday rental in Windham

Clean Condo w/ Loft 2 Mi to Windham Mountain Ski!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Mountain Condo, holiday rental in Windham
Cozy Mountain Condo, holiday rental in Windham
Cozy Mountain Condo, holiday rental in Windham

Cozy Mountain Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Newly Built 1200sq ft Guest House 4min to Ski & Hiking, holiday rental in Windham
Newly Built 1200sq ft Guest House 4min to Ski & Hiking, holiday rental in Windham
Newly Built 1200sq ft Guest House 4min to Ski & Hiking, holiday rental in Windham

Newly Built 1200sq ft Guest House 4min to Ski & Hiking

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Catskills Getaway w/ Yard & Mtn Views!, holiday rental in Windham
Cozy Catskills Getaway w/ Yard & Mtn Views!, holiday rental in Windham
Cozy Catskills Getaway w/ Yard & Mtn Views!, holiday rental in Windham

Cozy Catskills Getaway w/ Yard & Mtn Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ski house in Windham near Hunter and Windham mountains, holiday rental in Windham
Ski house in Windham near Hunter and Windham mountains, holiday rental in Windham
Ski house in Windham near Hunter and Windham mountains, holiday rental in Windham

Ski house in Windham near Hunter and Windham mountains

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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5 Minutes from Windham Mountain, holiday rental in Windham
5 Minutes from Windham Mountain, holiday rental in Windham
5 Minutes from Windham Mountain, holiday rental in Windham

5 Minutes from Windham Mountain

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!, holiday rental in Windham
Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!, holiday rental in Windham
Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!, holiday rental in Windham

Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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2 Bed Ski-In/Out Condo, holiday rental in Windham
2 Bed Ski-In/Out Condo, holiday rental in Windham
2 Bed Ski-In/Out Condo, holiday rental in Windham

2 Bed Ski-In/Out Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Haüs Windham - Luxury 2 Bedroom Suite w Loft, holiday rental in Windham
The Haüs Windham - Luxury 2 Bedroom Suite w Loft, holiday rental in Windham
The Haüs Windham - Luxury 2 Bedroom Suite w Loft, holiday rental in Windham

The Haüs Windham - Luxury 2 Bedroom Suite w Loft

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Windham Mountain Village Townhouse, holiday rental in Windham
Windham Mountain Village Townhouse, holiday rental in Windham
Windham Mountain Village Townhouse, holiday rental in Windham

Windham Mountain Village Townhouse

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo, holiday rental in Windham
Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo, holiday rental in Windham
Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo, holiday rental in Windham

Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relaxing Catskills Apt <3 Mi to Windham Mountain!, holiday rental in Windham
Relaxing Catskills Apt <3 Mi to Windham Mountain!, holiday rental in Windham
Relaxing Catskills Apt <3 Mi to Windham Mountain!, holiday rental in Windham

Relaxing Catskills Apt <3 Mi to Windham Mountain!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Showing results 1-50 of 203
Frequently Asked Questions about Windham