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Windham Holiday Rentals

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64 rentals in Windham.
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Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub
3 bedrooms
2 bathrooms
Sleeps 6
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Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain
9 bedrooms
5 bathrooms
Sleeps 30
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*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw
4 bedrooms
2 bathrooms
Sleeps 8
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Windham Log Cabin on 35 Acres
6 bedrooms
5 bathrooms
Sleeps 16
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Windham Mtn.-Walking distance to trail and base lodge!
4 bedrooms
3 bathrooms
Sleeps 12
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Winsome Windham - Secluded Chalet with Ski Windham Views
4 bedrooms
2 bathrooms
Sleeps 14
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Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham
1 bedroom
1 bathroom
Sleeps 2
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Windham: Fall & Winter now booking! High Speed WIFI, Private deck, Watch Video!
4 bedrooms
2 bathrooms
Sleeps 8
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****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!
4 bedrooms
4 bathrooms
Sleeps 10
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Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain
2 bedrooms
1 bathroom
Sleeps 6
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Spacious Retreat with Luxurious View
5 bedrooms
5 bathrooms
Sleeps 16
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Windham Quads Condo! Ski '20/'21. Scroll to bottom for Rates ⬇️
2 bedrooms
2 bathrooms
Sleeps 8
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'New Home' Idyllic Mt Views ,Pond & Horse farm views 2 min to Town
4 bedrooms
3 bathrooms
Sleeps 10
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Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet
2 bedrooms
3 bathrooms
Sleeps 6
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Windham Family Getaway (Brand New!)
3 bedrooms
2 bathrooms
Sleeps 9
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Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental
1 bedroom
1 bathroom
Sleeps 3
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Mountain House Retreat
5 bedrooms
2 bathrooms
Sleeps 10
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Beautiful Home, Gorgeous View, Spacious Living
3 bedrooms
2 bathrooms
Sleeps 10
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Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!
1 bedroom
1 bathroom
Sleeps 4
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'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!
12 bedrooms
10 bathrooms
Sleeps 33
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Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo
2 bedrooms
2 bathrooms
Sleeps 8
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Windham Mountain Getaway 2BD 2BA Condo
2 bedrooms
2 bathrooms
Sleeps 6
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The perfect mountain getaway nestled in the woods 2 min from downtown Windham.
4 bedrooms
3 bathrooms
Sleeps 15
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Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham
4 bedrooms
3 bathrooms
Sleeps 10
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NEW! Luxury Home on Windham Mountain! Walk to Slopes
4 bedrooms
4 bathrooms
Sleeps 11
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Secluded Charming Water Front Log Home
4 bedrooms
2 bathrooms
Sleeps 15
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5-Star Luxury Condo On Mountain: Ski-in & Ski-out
4 bedrooms
4 bathrooms
Sleeps 10
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Year-Round Relaxing Mountain Escape
5 bedrooms
4 bathrooms
Sleeps 10
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WINDHAM MAGNIFICENT HOLIDAY GETAWAY
5 bedrooms
4 bathrooms
Sleeps 18
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Escape Winter... above & beyond. Perfect house for family, friends & fresh air.
3 bedrooms
2 bathrooms
Sleeps 10
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Cute Condo in The Quads at Windham
1 bedroom
1 bathroom
Sleeps 4
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Modern Mountain House 5Bd/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn
5 bedrooms
3 bathrooms
Sleeps 12
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The Presidential Suite at Brie & Bordeaux
3 bedrooms
2 bathrooms
Sleeps 6
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Luxury Ski Windham Resort directly on Ski Mountain. Enjoy direct ski in/out
6 bedrooms
4 bathrooms
Sleeps 15
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***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***
2 bedrooms
2 bathrooms
Sleeps 5
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Amazing 4 BR on Windham
4 bedrooms
4 bathrooms
Sleeps 8
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Restored Firehouse w/Theater & Private Lake Access
4 bedrooms
2 bathrooms
Sleeps 18
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Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain
3 bedrooms
1 bathroom
Sleeps 7
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Spacious Mountain Escape - Minutes to Windham/Hunter
5 bedrooms
4 bathrooms
Sleeps 12
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Windham Townhouse - Base of Mountain
3 bedrooms
3 bathrooms
Sleeps 8
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Two-Story, 3-Bedroom Family Home
3 bedrooms
1 bathroom
Sleeps 4
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'The Mountain House' Windham Retreat w/ Hot Tub!
4 bedrooms
2 bathrooms
Sleeps 10
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The Mountain House: The Perfect 4 Season Retreat
8 bedrooms
7 bathrooms
Sleeps 22
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Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.
4 bedrooms
3 bathrooms
Sleeps 10
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Windham Mountain Ski House with Great Views
3 bedrooms
2 bathrooms
Sleeps 8
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Cristal pound at Windham ski resort
4 bedrooms
4 bathrooms
Sleeps 10
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The Xenia
4 bedrooms
3 bathrooms
Sleeps 16
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Windham Mountain Ski House
5 bedrooms
4 bathrooms
Sleeps 10
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Rare Ski Mountain View!
5 bedrooms
6 bathrooms
Sleeps 12
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NEW! Cozy Condo: Hike & Ski the Catskill Mountains
2 bedrooms
1 bathroom
Sleeps 4
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