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Windham Holiday Apartments

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59 rentals in Windham.
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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

3 bedrooms
2 bathrooms
Sleeps 6
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

9 bedrooms
5 bathrooms
Sleeps 30
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

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

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

4 bedrooms
4 bathrooms
Sleeps 10
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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Windham:  Ski Season: Wkds & Midweek- High Speed WIFI, Private deck, Watch Video, holiday rental in Windham

Windham: Ski Season: Wkds & Midweek- High Speed WIFI, Private deck, Watch Video

4 bedrooms
2 bathrooms
Sleeps 8
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!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Winsome Windham - Secluded Chalet with Ski Windham Views, holiday rental in Windham

Winsome Windham - Secluded Chalet with Ski Windham Views

4 bedrooms
2 bathrooms
Sleeps 14
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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Retreat with Luxurious View, holiday rental in Windham

Spacious Retreat with Luxurious View

5 bedrooms
5 bathrooms
Sleeps 16
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.

4 bedrooms
3 bathrooms
Sleeps 15
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

4 bedrooms
4 bathrooms
Sleeps 10
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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Windham Quads Condo! Ski '20/'21. Scroll to bottom for Rates ⬇️, holiday rental in Windham

Windham Quads Condo! Ski '20/'21. Scroll to bottom for Rates ⬇️

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Windham Family Getaway (Brand New!), holiday rental in Windham

Windham Family Getaway (Brand New!)

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Escape Winter... above & beyond. Perfect house for family, friends & fresh air., holiday rental in Windham

Escape Winter... above & beyond. Perfect house for family, friends & fresh air.

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Windham Mountain Getaway 2BD 2BA Condo, holiday rental in Windham

Windham Mountain Getaway 2BD 2BA Condo

2 bedrooms
2 bathrooms
Sleeps 6
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

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Year-Round Relaxing Mountain Escape, holiday rental in Windham

Year-Round Relaxing Mountain Escape

5 bedrooms
4 bathrooms
Sleeps 10
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

1 bedroom
1 bathroom
Sleeps 3
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!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Mountain House Retreat, holiday rental in Windham

Mountain House Retreat

5 bedrooms
2 bathrooms
Sleeps 10
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

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Charming Water Front Log Home, holiday rental in Windham

Secluded Charming Water Front Log Home

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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NEW! Luxury Home on Windham Mountain! Walk to Slopes, holiday rental in Windham

NEW! Luxury Home on Windham Mountain! Walk to Slopes

4 bedrooms
4 bathrooms
Sleeps 11
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

5 bedrooms
3 bathrooms
Sleeps 12
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

2 bedrooms
1 bathroom
Sleeps 4
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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Windham Townhouse - Base of Mountain, holiday rental in Windham

Windham Townhouse - Base of Mountain

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Presidential Suite at Brie & Bordeaux, holiday rental in Windham

The Presidential Suite at Brie & Bordeaux

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***, holiday rental in Windham

***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Luxury Ski Windham Resort directly on Ski Mountain. Enjoy direct ski in/out, holiday rental in Windham

Luxury Ski Windham Resort directly on Ski Mountain. Enjoy direct ski in/out

6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain, holiday rental in Windham

Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Spacious Mountain Escape - Minutes to Windham/Hunter, holiday rental in Windham

Spacious Mountain Escape - Minutes to Windham/Hunter

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Luxe Windham Home w/Hot Tub - Walk to Ski Resort!, holiday rental in Windham

Luxe Windham Home w/Hot Tub - Walk to Ski Resort!

8 bedrooms
3 bathrooms
Sleeps 17
Match: Sleeps
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On Windham Mountain - Westside Chalet, holiday rental in Windham

On Windham Mountain - Westside Chalet

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Windham Mountain Ski House with Great Views, holiday rental in Windham

Windham Mountain Ski House with Great Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Cozy Catskills Getaway w/ Yard & Mtn Views!, holiday rental in Windham

NEW! Cozy Catskills Getaway w/ Yard & Mtn Views!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Two-Story, 3-Bedroom Family Home, holiday rental in Windham

Two-Story, 3-Bedroom Family Home

3 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!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Mountain House: The Perfect 4 Season Retreat, holiday rental in Windham

The Mountain House: The Perfect 4 Season Retreat

8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Tentrr Signature Site - Pleasant Valley Maplecroft Camp, holiday rental in Windham

Tentrr Signature Site - Pleasant Valley Maplecroft Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Luxe Family Home 2Mi to Windham Mountain & Resort, holiday rental in Windham

Luxe Family Home 2Mi to Windham Mountain & Resort

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Modern & Cozy Windham Mountain Home: Hike & Tennis, holiday rental in Windham

Modern & Cozy Windham Mountain Home: Hike & Tennis

6 bedrooms
4 bathrooms
Sleeps 12
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!

2 bedrooms
1 bathroom
Sleeps 4
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!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chickadee Chalet, holiday rental in Windham

Chickadee Chalet

2 bedrooms
1 bathroom
Sleeps 4
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!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Stylish Mtn Escape w/ Hot Tub, 3 Miles to Ski, holiday rental in Windham

NEW! Stylish Mtn Escape w/ Hot Tub, 3 Miles to Ski

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fish, Golf, Bike, Hike; steps to Windham Ski resort., holiday rental in Windham

Fish, Golf, Bike, Hike; steps to Windham Ski resort.

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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