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Windham Family & Kid Friendly Rentals

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52 rentals in Windham.
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Mountain House Retreat
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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33 other travelers have booked this property
*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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28 other travelers have booked this property
Mountain Treasure Cottage, WIndham, NY
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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14 other travelers have booked this property
***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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1 other traveler has booked this property
The Presidential Suite at Brie & Bordeaux
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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2 other travelers have booked this property
Windham Mountain Ski House with Great Views
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Two-Story, 3-Bedroom Family Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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The Mountain House: The Perfect 4 Season Retreat
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps, Kid friendly
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Enjoy any season at this beautiful townhouse in Windham
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Windham: June AVAIL! High Speed WIFI, Private deck, Watch Video!
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Windham Log Cabin on 35 Acres
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps, Kid friendly
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Winsome Windham - Secluded Chalet with Ski Windham Views
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps, Kid friendly
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Windham Mtn.-Walking distance to trail and base lodge!
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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WINDHAM MAGNIFICENT HOLIDAY GETAWAY
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps, Kid friendly
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Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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2 other travelers have booked this property
Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain
9 bedrooms
5 bathrooms
Sleeps 30
Match: Sleeps, Kid friendly
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Windham Mountain Ski House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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'The Mountain House' Windham Retreat w/ Hot Tub!
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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The Xenia
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps, Kid friendly
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1 other traveler has booked this property
Secluded Charming Water Front Log Home
4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps, Kid friendly
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13 other travelers have booked this property
Amazing 4 BR on Windham
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Restored Firehouse w/Theater & Private Lake Access
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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1 other traveler has booked this property
Charming Mountain Retreat Lg Modern Kitchen on Stream w Fire-pit
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Rare Ski Mountain View!
5 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps, Kid friendly
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Windham Townhouse - Base of Mountain
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Cute Condo in The Quads at Windham
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Windham Quads Condominium! Spring & Summer 2020. Scroll to bottom for Rates ⬇️
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Spacious House - 1 Mi. to Windham Ski Resort!
5 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps, Kid friendly
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'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!
12 bedrooms
10 bathrooms
Sleeps 33
Match: Sleeps, Kid friendly
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Modern Home w/ Deck, 5 Minutes to Windham Resort!
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Kid friendly
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Tentrr Signature Site - Pleasant Valley Maplecroft Camp
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Windham Mountain Escape - Pool! Tennis!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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NEW! Luxury Home on Windham Mountain! Walk to Slopes
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps, Kid friendly
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'New Home' Idyllic Mt Views ,Pond & Horse farm views 2 min to Town
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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'NEW'LUXURY SKI-IN SKI-OUT ALPINE CHALET at WINDHAM MOUNTAIN...WEDDINGS WELCOME
7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Beautiful Home, Gorgeous View, Spacious Living
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Fish, Golf, Bike, Hike; steps to Windham Ski resort.
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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Luxe Windham Home w/Hot Tub - Walk to Ski Resort!
8 bedrooms
3 bathrooms
Sleeps 17
Match: Sleeps, Kid friendly
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The perfect mountain getaway nestled in the woods 2 min from downtown Windham.
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps, Kid friendly
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****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Windham Family Getaway (Brand New!)
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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5-Star Luxury Condo On Mountain: Ski-in & Ski-out
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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NEW! Condo w/Loft: 2 Miles to Windham Mountain Ski
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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NEW! Cozy Condo: Hike & Ski the Catskill Mountains
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Catskills House w/Yard, 1Mi to Windham Mtn Resort!
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Modern Mountain House 5Bd/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Gorgeous, First Class, 2 King apartment in downtown Windham
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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