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Cheap Windham Holiday Homes

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
191 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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Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter, holiday rental in Windham
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter, holiday rental in Windham
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter, holiday rental in Windham

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

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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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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Luxury Log Cabin-Windham Mountain.  Amazing sunsets, large lawn, deck, fireplace, holiday rental in Windham
Luxury Log Cabin-Windham Mountain.  Amazing sunsets, large lawn, deck, fireplace, holiday rental in Windham
Luxury Log Cabin-Windham Mountain.  Amazing sunsets, large lawn, deck, fireplace, holiday rental in Windham

Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace

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

NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Redwood Retreat in Windham - Pickleball! Tennis!, holiday rental in Windham
Redwood Retreat in Windham - Pickleball! Tennis!, holiday rental in Windham
Redwood Retreat in Windham - Pickleball! Tennis!, holiday rental in Windham

Redwood Retreat in Windham - Pickleball! Tennis!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski Ridge Golf farmhouse, holiday rental in Windham
Ski Ridge Golf farmhouse, holiday rental in Windham
Ski Ridge Golf farmhouse, holiday rental in Windham

Ski Ridge Golf farmhouse

Holiday Rental House
4 bedrooms
4 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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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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NEW OUTDOOR HOT TUB!  1-Bedroom Luxury Suite + Full Kitch - Haus Windham, holiday rental in Windham
NEW OUTDOOR HOT TUB!  1-Bedroom Luxury Suite + Full Kitch - Haus Windham, holiday rental in Windham
NEW OUTDOOR HOT TUB!  1-Bedroom Luxury Suite + Full Kitch - Haus Windham, holiday rental in Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham, holiday rental in Windham
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham, holiday rental in Windham
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham, holiday rental in Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Guesthouse Minutes from the Mountain!, holiday rental in Windham
Guesthouse Minutes from the Mountain!, holiday rental in Windham
Guesthouse Minutes from the Mountain!, holiday rental in Windham

Guesthouse Minutes from the Mountain!

Holiday Rental House
1 bedroom
1 bathroom
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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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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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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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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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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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
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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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Immaculate Windham Getaway Near Skiing & Hiking!, holiday rental in Windham
Immaculate Windham Getaway Near Skiing & Hiking!, holiday rental in Windham
Immaculate Windham Getaway Near Skiing & Hiking!, holiday rental in Windham

Immaculate Windham Getaway Near Skiing & Hiking!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountain view apartment, 5mins to Ski Area!, holiday rental in Windham
Mountain view apartment, 5mins to Ski Area!, holiday rental in Windham
Mountain view apartment, 5mins to Ski Area!, holiday rental in Windham

Mountain view apartment, 5mins to Ski Area!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Catskills Home, 5 Mins to Windham Mtn Resort!, holiday rental in Windham
Catskills Home, 5 Mins to Windham Mtn Resort!, holiday rental in Windham
Catskills Home, 5 Mins to Windham Mtn Resort!, holiday rental in Windham

Catskills Home, 5 Mins to Windham Mtn Resort!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Apt w/ Yard: 3 Mi to Windham Mountain, holiday rental in Windham
Spacious Apt w/ Yard: 3 Mi to Windham Mountain, holiday rental in Windham
Spacious Apt w/ Yard: 3 Mi to Windham Mountain, holiday rental in Windham

Spacious Apt w/ Yard: 3 Mi to Windham Mountain

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CONVENIENT!Walk 1000ft. to Windham Mtn! Fully furnished 2BR/2Bth Condo w/WiFi, holiday rental in Windham
CONVENIENT!Walk 1000ft. to Windham Mtn! Fully furnished 2BR/2Bth Condo w/WiFi, holiday rental in Windham
CONVENIENT!Walk 1000ft. to Windham Mtn! Fully furnished 2BR/2Bth Condo w/WiFi, holiday rental in Windham

CONVENIENT!Walk 1000ft. to Windham Mtn! Fully furnished 2BR/2Bth Condo w/WiFi

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy townhouse steps away from Windham Mountain-  zip code 12496, holiday rental in Windham
Cozy townhouse steps away from Windham Mountain-  zip code 12496, holiday rental in Windham
Cozy townhouse steps away from Windham Mountain-  zip code 12496, holiday rental in Windham

Cozy townhouse steps away from Windham Mountain- zip code 12496

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Foot of fresh SNOW Amazing skiing & snowboarding, holiday rental in Windham
Foot of fresh SNOW Amazing skiing & snowboarding, holiday rental in Windham
Foot of fresh SNOW Amazing skiing & snowboarding, holiday rental in Windham

Foot of fresh SNOW Amazing skiing & snowboarding

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ski Windham House Family Friendly!, holiday rental in Windham
Ski Windham House Family Friendly!, holiday rental in Windham
Ski Windham House Family Friendly!, holiday rental in Windham

Ski Windham House Family Friendly!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Windham castle with a view & minutes to skiing!, holiday rental in Windham
Windham castle with a view & minutes to skiing!, holiday rental in Windham
Windham castle with a view & minutes to skiing!, holiday rental in Windham

Windham castle with a view & minutes to skiing!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Windham family ski home, walking distance to trails and base, holiday rental in Windham
Windham family ski home, walking distance to trails and base, holiday rental in Windham
Windham family ski home, walking distance to trails and base, holiday rental in Windham

Windham family ski home, walking distance to trails and base

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Serenity w/ Hot Tub & Fireplace 3 min to town, holiday rental in Windham
Serenity w/ Hot Tub & Fireplace 3 min to town, holiday rental in Windham
Serenity w/ Hot Tub & Fireplace 3 min to town, holiday rental in Windham

Serenity w/ Hot Tub & Fireplace 3 min to town

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mid Century Modern Chalet with Tennis Court and Catskill Views, holiday rental in Windham
Mid Century Modern Chalet with Tennis Court and Catskill Views, holiday rental in Windham
Mid Century Modern Chalet with Tennis Court and Catskill Views, holiday rental in Windham

Mid Century Modern Chalet with Tennis Court and Catskill Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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4 bedroom house 10 minutes to Windham Mountain, holiday rental in Windham
4 bedroom house 10 minutes to Windham Mountain, holiday rental in Windham
4 bedroom house 10 minutes to Windham Mountain, holiday rental in Windham

4 bedroom house 10 minutes to Windham Mountain

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Windham resort area. Pet friendly home with mountain views, near hiking trails., holiday rental in Windham
Windham resort area. Pet friendly home with mountain views, near hiking trails., holiday rental in Windham
Windham resort area. Pet friendly home with mountain views, near hiking trails., holiday rental in Windham

Windham resort area. Pet friendly home with mountain views, near hiking trails.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Above & beyond.  Perfect house for family, friends & fresh air., holiday rental in Windham
Above & beyond.  Perfect house for family, friends & fresh air., holiday rental in Windham
Above & beyond.  Perfect house for family, friends & fresh air., holiday rental in Windham

Above & beyond. Perfect house for family, friends & fresh air.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Windham Pines Lodge & Hot Tub, holiday rental in Windham
Windham Pines Lodge & Hot Tub, holiday rental in Windham
Windham Pines Lodge & Hot Tub, holiday rental in Windham

Windham Pines Lodge & Hot Tub

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Windham Mountain A Frame Ski House with Central A/C, holiday rental in Windham
Windham Mountain A Frame Ski House with Central A/C, holiday rental in Windham
Windham Mountain A Frame Ski House with Central A/C, holiday rental in Windham

Windham Mountain A Frame Ski House with Central A/C

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Restored Firehouse One Minute to Skiing on Main St, holiday rental in Windham
Restored Firehouse One Minute to Skiing on Main St, holiday rental in Windham
Restored Firehouse One Minute to Skiing on Main St, holiday rental in Windham

Restored Firehouse One Minute to Skiing on Main St

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 18
Match: Sleeps
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Luxury Home w/ Deck: Explore the Catskill Mtns!, holiday rental in Windham
Luxury Home w/ Deck: Explore the Catskill Mtns!, holiday rental in Windham
Luxury Home w/ Deck: Explore the Catskill Mtns!, holiday rental in Windham

Luxury Home w/ Deck: Explore the Catskill Mtns!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too., holiday rental in Windham
Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too., holiday rental in Windham
Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too., holiday rental in Windham

Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Mountain Contemporary, minutes to slopes with breathtaking views!, holiday rental in Windham
Mountain Contemporary, minutes to slopes with breathtaking views!, holiday rental in Windham
Mountain Contemporary, minutes to slopes with breathtaking views!, holiday rental in Windham

Mountain Contemporary, minutes to slopes with breathtaking views!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Steps away from the magic carpet that brings you right to the lodge!, holiday rental in Windham
Steps away from the magic carpet that brings you right to the lodge!, holiday rental in Windham
Steps away from the magic carpet that brings you right to the lodge!, holiday rental in Windham

Steps away from the magic carpet that brings you right to the lodge!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM, holiday rental in Windham
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM, holiday rental in Windham
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM, holiday rental in Windham

NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Windham Mountain Vacation Rental ~3 Mi to Lifts!, holiday rental in Windham
Windham Mountain Vacation Rental ~3 Mi to Lifts!, holiday rental in Windham
Windham Mountain Vacation Rental ~3 Mi to Lifts!, holiday rental in Windham

Windham Mountain Vacation Rental ~3 Mi to Lifts!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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