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Windham Condos

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171 rentals in Windham.
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Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, vacation rental in Windham
Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, vacation rental in Windham
Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, vacation rental in Windham

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain, vacation rental in Windham
Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain, vacation rental in Windham
Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain, vacation rental in Windham

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

Rental Home
9 bedrooms
5 bathrooms
Sleeps 30
Match: Sleeps
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FRESH SNOWSTORM Cutest Cabin in Windham for 2 People, vacation rental in Windham
FRESH SNOWSTORM Cutest Cabin in Windham for 2 People, vacation rental in Windham
FRESH SNOWSTORM Cutest Cabin in Windham for 2 People, vacation rental in Windham

FRESH SNOWSTORM Cutest Cabin in Windham for 2 People

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury Log Home with Ski Windham views, vacation rental in Windham
Luxury Log Home with Ski Windham views, vacation rental in Windham
Luxury Log Home with Ski Windham views, vacation rental in Windham

Luxury Log Home with Ski Windham views

Rental Home
4 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw, vacation rental in Windham
*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw, vacation rental in Windham
*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw, vacation rental in Windham

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Windham Log Cabin on 35 Acres, vacation rental in Windham
Windham Log Cabin on 35 Acres, vacation rental in Windham
Windham Log Cabin on 35 Acres, vacation rental in Windham

Windham Log Cabin on 35 Acres

Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!, vacation rental in Windham
'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!, vacation rental in Windham
'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!, vacation rental in Windham

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

Rental Home
12 bedrooms
10 bathrooms
Sleeps 33
Match: Sleeps
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DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet, vacation rental in Windham
DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet, vacation rental in Windham
DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet, vacation rental in Windham

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham, vacation rental in Windham
Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham, vacation rental in Windham
Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham, vacation rental in Windham

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

Cabin
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Timber frame home 5 minutes from Windham Mountain.  Perfect for 2 families!, vacation rental in Windham
Timber frame home 5 minutes from Windham Mountain.  Perfect for 2 families!, vacation rental in Windham
Timber frame home 5 minutes from Windham Mountain.  Perfect for 2 families!, vacation rental in Windham

Timber frame home 5 minutes from Windham Mountain. Perfect for 2 families!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain, vacation rental in Windham
Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain, vacation rental in Windham
Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain, vacation rental in Windham

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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5-Star Luxury Condo On Mountain: Ski-in & Ski-out, vacation rental in Windham
5-Star Luxury Condo On Mountain: Ski-in & Ski-out, vacation rental in Windham
5-Star Luxury Condo On Mountain: Ski-in & Ski-out, vacation 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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Ski Windham House Family Friendly!, vacation rental in Windham
Ski Windham House Family Friendly!, vacation rental in Windham
Ski Windham House Family Friendly!, vacation rental in Windham

Ski Windham House Family Friendly!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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*4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*2 WEBERs*Windhm Mtn Views*, vacation rental in Windham
*4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*2 WEBERs*Windhm Mtn Views*, vacation rental in Windham
*4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*2 WEBERs*Windhm Mtn Views*, vacation rental in Windham

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond, vacation rental in Windham
5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond, vacation rental in Windham
5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond, vacation rental in Windham

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

Rental Home
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Windham Condominium! Strong Private WiFi! 2BR/2B, Sleeps 6-8 ⬇️, vacation rental in Windham
Windham Condominium! Strong Private WiFi! 2BR/2B, Sleeps 6-8 ⬇️, vacation rental in Windham
Windham Condominium! Strong Private WiFi! 2BR/2B, Sleeps 6-8 ⬇️, vacation rental in Windham

Windham Condominium! Strong Private WiFi! 2BR/2B, Sleeps 6-8 ⬇️

Condo/Apartment
2 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., vacation rental in Windham
Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too., vacation rental in Windham
Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too., vacation rental in Windham

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Windham Mtn.-Walking distance to trail and base lodge!, vacation rental in Windham
Windham Mtn.-Walking distance to trail and base lodge!, vacation rental in Windham
Windham Mtn.-Walking distance to trail and base lodge!, vacation rental in Windham

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Windham:  Ski Weeks/Wknds Avail! High Speed WIFI, Private deck, Watch Video, vacation rental in Windham
Windham:  Ski Weeks/Wknds Avail! High Speed WIFI, Private deck, Watch Video, vacation rental in Windham
Windham:  Ski Weeks/Wknds Avail! High Speed WIFI, Private deck, Watch Video, vacation rental in Windham

Windham: Ski Weeks/Wknds Avail! High Speed WIFI, Private deck, Watch Video

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!, vacation rental in Windham
****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!, vacation rental in Windham
****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!, vacation rental in Windham

****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Ultra Clean, Modern, Close to Windham Mountain... Available tonight, Book Now!., vacation rental in Windham
Ultra Clean, Modern, Close to Windham Mountain... Available tonight, Book Now!., vacation rental in Windham
Ultra Clean, Modern, Close to Windham Mountain... Available tonight, Book Now!., vacation rental in Windham

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

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

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities, vacation rental in Windham
Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities, vacation rental in Windham
Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities, vacation rental in Windham

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home, vacation rental in Windham
The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home, vacation rental in Windham
The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home, vacation rental in Windham

The Xenia - A 4 Seasons Family Friendly Spacious Mountain Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, vacation rental in Windham
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, vacation rental in Windham
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!, vacation rental in Windham

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Spacious Retreat with Luxurious View, vacation rental in Windham
Spacious Retreat with Luxurious View, vacation rental in Windham
Spacious Retreat with Luxurious View, vacation rental in Windham

Spacious Retreat with Luxurious View

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Windham Private heated indoor pool., vacation rental in Windham
Windham Private heated indoor pool., vacation rental in Windham
Windham Private heated indoor pool., vacation rental in Windham

Windham Private heated indoor pool.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Mountain House Retreat, vacation rental in Windham
Mountain House Retreat, vacation rental in Windham
Mountain House Retreat, vacation rental in Windham

Mountain House Retreat

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Windham Family Getaway, vacation rental in Windham
Windham Family Getaway, vacation rental in Windham
Windham Family Getaway, vacation rental in Windham

Windham Family Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Year-Round Relaxing Mountain Escape, vacation rental in Windham
Year-Round Relaxing Mountain Escape, vacation rental in Windham
Year-Round Relaxing Mountain Escape, vacation rental in Windham

Year-Round Relaxing Mountain Escape

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Above & beyond. Perfect house for family, friends & fresh air., vacation rental in Windham
Above & beyond. Perfect house for family, friends & fresh air., vacation rental in Windham
Above & beyond. Perfect house for family, friends & fresh air., vacation 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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Foot of fresh SNOW Amazing skiing & snowboarding, vacation rental in Windham
Foot of fresh SNOW Amazing skiing & snowboarding, vacation rental in Windham
Foot of fresh SNOW Amazing skiing & snowboarding, vacation rental in Windham

Foot of fresh SNOW Amazing skiing & snowboarding

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet, vacation rental in Windham
Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet, vacation rental in Windham
Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet, vacation rental in Windham

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

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

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental , vacation rental in Windham
Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental , vacation rental in Windham
Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental , vacation 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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'New Home' Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, vacation rental in Windham
'New Home' Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, vacation rental in Windham
'New Home' Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, vacation rental in Windham

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ready for your family if you need a retreat., vacation rental in Windham
Ready for your family if you need a retreat., vacation rental in Windham
Ready for your family if you need a retreat., vacation rental in Windham

Ready for your family if you need a retreat.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Home on Windham Mountain! Walk to Slopes, vacation rental in Windham
Luxury Home on Windham Mountain! Walk to Slopes, vacation rental in Windham
Luxury Home on Windham Mountain! Walk to Slopes, vacation rental in Windham

Luxury Home on Windham Mountain! Walk to Slopes

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

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!, vacation rental in Windham
Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!, vacation rental in Windham
Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!, vacation rental in Windham

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Redwood Retreat in Windham - Pool! Tennis!, vacation rental in Windham
Redwood Retreat in Windham - Pool! Tennis!, vacation rental in Windham
Redwood Retreat in Windham - Pool! Tennis!, vacation rental in Windham

Redwood Retreat in Windham - Pool! Tennis!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'The Mountain House' Windham Retreat w/ Hot Tub!, vacation rental in Windham
'The Mountain House' Windham Retreat w/ Hot Tub!, vacation rental in Windham
'The Mountain House' Windham Retreat w/ Hot Tub!, vacation rental in Windham

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Windham Townhouse - Base of Mountain, vacation rental in Windham
Windham Townhouse - Base of Mountain, vacation rental in Windham
Windham Townhouse - Base of Mountain, vacation rental in Windham

Windham Townhouse - Base of Mountain

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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PENTHOUSE /Sun Room, deck, Mountain view, 5 beds sleeps 7, vacation rental in Windham
PENTHOUSE /Sun Room, deck, Mountain view, 5 beds sleeps 7, vacation rental in Windham
PENTHOUSE /Sun Room, deck, Mountain view, 5 beds sleeps 7, vacation rental in Windham

PENTHOUSE /Sun Room, deck, Mountain view, 5 beds sleeps 7

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Mountain House Retreat, vacation rental in Windham
Mountain House Retreat, vacation rental in Windham
Mountain House Retreat, vacation rental in Windham

Mountain House Retreat

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Windham ski house!  4 miles to Windham Mtn!, vacation rental in Windham
Windham ski house!  4 miles to Windham Mtn!, vacation rental in Windham
Windham ski house!  4 miles to Windham Mtn!, vacation rental in Windham

Windham ski house! 4 miles to Windham Mtn!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy townhouse steps away from Windham Mountain-  zip code 12496, vacation rental in Windham
Cozy townhouse steps away from Windham Mountain-  zip code 12496, vacation rental in Windham
Cozy townhouse steps away from Windham Mountain-  zip code 12496, vacation rental in Windham

Cozy townhouse steps away from Windham Mountain- zip code 12496

Rental Home
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful home, beautiful views, spacious living room, vacation rental in Windham
Beautiful home, beautiful views, spacious living room, vacation rental in Windham
Beautiful home, beautiful views, spacious living room, vacation rental in Windham

Beautiful home, beautiful views, spacious living room

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Ski season 2022/23  nov-15 to april 1, 2023, vacation rental in Windham
Ski season 2022/23  nov-15 to april 1, 2023, vacation rental in Windham
Ski season 2022/23  nov-15 to april 1, 2023, vacation rental in Windham

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo, vacation rental in Windham
Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo, vacation rental in Windham
Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo, vacation 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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