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Holiday Rentals in Windham

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181 rentals in Windham.
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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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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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DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet, holiday rental in Windham
DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet, holiday rental in Windham
DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet, holiday rental in Windham

DREAM LOG CABIN 110 Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain, holiday rental in Windham
Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain, holiday rental in Windham
Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain, holiday rental in Windham

Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain

Holiday Rental House
9 bedrooms
5 bathrooms
Sleeps 30
Match: Sleeps
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Windham:  Ski Weeks & Weekends AVAIL!  High Speed WIFI, Close to Mountain, holiday rental in Windham
Windham:  Ski Weeks & Weekends AVAIL!  High Speed WIFI, Close to Mountain, holiday rental in Windham
Windham:  Ski Weeks & Weekends AVAIL!  High Speed WIFI, Close to Mountain, holiday rental in Windham

Windham: Ski Weeks & Weekends AVAIL! High Speed WIFI, Close to Mountain

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw, holiday rental in Windham
*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw, holiday rental in Windham
*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw, holiday rental in Windham

*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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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Luxury Log Home with Ski Windham views, holiday rental in Windham
Luxury Log Home with Ski Windham views, holiday rental in Windham
Luxury Log Home with Ski Windham views, holiday rental in Windham

Luxury Log Home with Ski Windham views

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Windham Mtn.-Walking distance to trail and base lodge!, holiday rental in Windham
Windham Mtn.-Walking distance to trail and base lodge!, holiday rental in Windham
Windham Mtn.-Walking distance to trail and base lodge!, holiday rental in Windham

Windham Mtn.-Walking distance to trail and base lodge!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
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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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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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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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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5-Star Luxury Condo On Mountain: Ski-in & Ski-out, holiday rental in Windham
5-Star Luxury Condo On Mountain: Ski-in & Ski-out, holiday rental in Windham
5-Star Luxury Condo On Mountain: Ski-in & Ski-out, holiday rental in Windham

5-Star Luxury Condo On Mountain: Ski-in & Ski-out

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond, holiday rental in Windham
5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond, holiday rental in Windham
5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond, holiday rental in Windham

5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain, holiday rental in Windham
Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain, holiday rental in Windham
Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain, holiday rental in Windham

Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities, holiday rental in Windham
Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities, holiday rental in Windham
Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities, holiday rental in Windham

Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
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 12
Match: Sleeps
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Retreat mountain home, holiday rental in Windham
Retreat mountain home, holiday rental in Windham
Retreat mountain home, holiday rental in Windham

Retreat mountain home

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet, holiday rental in Windham
Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet, holiday rental in Windham
Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet, holiday rental in Windham

Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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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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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*4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*2 WEBERs*Windhm Mtn Views*, holiday rental in Windham
*4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*2 WEBERs*Windhm Mtn Views*, holiday rental in Windham
*4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*2 WEBERs*Windhm Mtn Views*, holiday rental in Windham

*4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*2 WEBERs*Windhm Mtn Views*

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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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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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Ready for your family if you need a retreat., holiday rental in Windham
Ready for your family if you need a retreat., holiday rental in Windham
Ready for your family if you need a retreat., holiday rental in Windham

Ready for your family if you need a retreat.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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"New Home" Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, holiday rental in Windham
"New Home" Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, holiday rental in Windham
"New Home" Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, holiday rental in Windham

"New Home" Idyllic Mt Views ,Pond & Horse farm views 2 min to Town

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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3-Bedroom Family Home, holiday rental in Windham
3-Bedroom Family Home, holiday rental in Windham
3-Bedroom Family Home, holiday rental in Windham

3-Bedroom Family Home

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!, holiday rental in Windham
'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!, holiday rental in Windham
'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!, holiday rental in Windham

'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!

Holiday Rental House
12 bedrooms
10 bathrooms
Sleeps 33
Match: Sleeps
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Ultra Clean, Modern, Close to Windham Mountain... Available tonight, Book Now!., holiday rental in Windham
Ultra Clean, Modern, Close to Windham Mountain... Available tonight, Book Now!., holiday rental in Windham
Ultra Clean, Modern, Close to Windham Mountain... Available tonight, Book Now!., holiday rental in Windham

Ultra Clean, Modern, Close to Windham Mountain... Available tonight, Book Now!.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, holiday rental in Windham
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, holiday rental in Windham
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, holiday rental in Windham

ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 13
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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Windham Family Getaway, holiday rental in Windham
Windham Family Getaway, holiday rental in Windham
Windham Family Getaway, holiday rental in Windham

Windham Family Getaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
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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ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, holiday rental in Windham
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, holiday rental in Windham
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, holiday rental in Windham

ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Year-Round Relaxing Mountain Escape, holiday rental in Windham
Year-Round Relaxing Mountain Escape, holiday rental in Windham
Year-Round Relaxing Mountain Escape, holiday rental in Windham

Year-Round Relaxing Mountain Escape

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Ski season 2022/23  nov-15 to april 1, 2023, holiday rental in Windham
Ski season 2022/23  nov-15 to april 1, 2023, holiday rental in Windham
Ski season 2022/23  nov-15 to april 1, 2023, holiday rental in Windham

Ski season 2022/23 nov-15 to april 1, 2023

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Retreat with Luxurious View, holiday rental in Windham
Spacious Retreat with Luxurious View, holiday rental in Windham
Spacious Retreat with Luxurious View, holiday rental in Windham

Spacious Retreat with Luxurious View

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
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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Tuscan Year Round Beauty / Weddings - Gatherings - Outdoor Kitchen - PickleBall, holiday rental in Windham
Tuscan Year Round Beauty / Weddings - Gatherings - Outdoor Kitchen - PickleBall, holiday rental in Windham
Tuscan Year Round Beauty / Weddings - Gatherings - Outdoor Kitchen - PickleBall, holiday rental in Windham

Tuscan Year Round Beauty / Weddings - Gatherings - Outdoor Kitchen - PickleBall

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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The perfect mountain getaway nestled in the woods 2 min from downtown Windham., holiday rental in Windham
The perfect mountain getaway nestled in the woods 2 min from downtown Windham., holiday rental in Windham
The perfect mountain getaway nestled in the woods 2 min from downtown Windham., holiday rental in Windham

The perfect mountain getaway nestled in the woods 2 min from downtown Windham.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 15
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.

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
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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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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Windham Condominium! 2BR/2B, Sleeps 6-8. Strong Private Wi-Fi! ⬇️, holiday rental in Windham
Windham Condominium! 2BR/2B, Sleeps 6-8. Strong Private Wi-Fi! ⬇️, holiday rental in Windham
Windham Condominium! 2BR/2B, Sleeps 6-8. Strong Private Wi-Fi! ⬇️, holiday rental in Windham

Windham Condominium! 2BR/2B, Sleeps 6-8. Strong Private Wi-Fi! ⬇️

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Home on Windham Mountain! Walk to Slopes, holiday rental in Windham
Luxury Home on Windham Mountain! Walk to Slopes, holiday rental in Windham
Luxury Home on Windham Mountain! Walk to Slopes, holiday rental in Windham

Luxury Home on Windham Mountain! Walk to Slopes

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham, holiday rental in Windham
Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham, holiday rental in Windham
Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham, holiday rental in Windham

Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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All Season Luxury Condo in Windham/ Ski On - Ski Off, holiday rental in Windham
All Season Luxury Condo in Windham/ Ski On - Ski Off, holiday rental in Windham
All Season Luxury Condo in Windham/ Ski On - Ski Off, holiday rental in Windham

All Season Luxury Condo in Windham/ Ski On - Ski Off

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 12
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
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Modern Mountain House 5Bd/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn, holiday rental in Windham
Modern Mountain House 5Bd/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn, holiday rental in Windham
Modern Mountain House 5Bd/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn, holiday rental in Windham

Modern Mountain House 5Bd/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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