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Holiday rentals in Windham County

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Top-rated holiday rentals in Windham County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cabin in Londonderry
Cozy après ski cabin with fire pit & hot tub
Deerwood Hill is a 3.6 acre base camp for all of your Green Mountain Southern Vermont adventures. Within 15 minutes to Stratton, Bromley, and Magic ski resorts! Also, under 30 minute drive to many restaurants and the shopping mecca that is Manchester! The beautiful surroundings of South Londonderry will not disappoint. *Comfortably sleeps 6! Guests must be 25+ (children with parents welcome). Please note that our 2nd bedroom is the upstairs open loft area w/ full bath.* *NO PARTIES OR PETS**
₹20,015 per night
Cabin in Newfane
Vermont Cabin - Amazing Views, Close to Mount Snow
Come stay in our sparkling clean, renovated log cabin in the woods with beautiful views of river, mountains and stars. Located by the charming village of Williamsville, close to historic Newfane village, 12 miles from Mount Snow for skiing, and right on the refreshingly cool and clear Rock River. It's the perfect place for a romantic getaway, a family vacation or quality times with dear friends. Just installed: outdoor hot tub with views of mountains, river and lots of open sky above.
₹18,591 per night
Rental unit in Dummerston
HeART Barn Retreat
This 1850's Barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. The West river trail is half a mile down the road where you can walk or bike along river which takes you into Brattleboro. A peaceful retreat to rest and explore. Mount Snow is 35 minutes away. Okemo and Stratton are both 1 hour away. *Please no smoking anywhere on the property.
₹6,944 per night

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Other great holiday rentals in Windham County

Guest house in Putney
Cozy cottage loft and retreat
₹8,169 per night
Barn in Marlboro
The Studio With a View. Bring your dog, too!
₹8,275 per night
Cabin in Wilmington
Alpine A-Frame - midcentury cabin by Lake Raponda
₹17,681 per night
Home in Jamaica
Green Mountain Tiny House: a mountainside retreat
₹12,359 per night
Cabin in Wardsboro
Mod Cabin in woods Hot Tub near Stratton & MtSnow
₹53,100 per night
Cabin in Londonderry
₹14,250 per night
Cabin in Stratton
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
₹14,728 per night
Cabin in Wardsboro
Log Cabin Near Stratton/Mt Snow
₹8,752 per night
Guest suite in Brattleboro
Charming studio in renovated 19th century church.
₹7,271 per night
Tiny home in Jamaica
Apple Blossom Cottage: A Tiny House
₹6,814 per night
Cabin in Wilmington
Peaceful Mt Snow Escape w/Hot Tub
₹30,202 per night
Cabin in Wardsboro
Mountain side acres
₹12,837 per night
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