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Family-friendly vacation rentals in Windham County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windham County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham County family-friendly rentals
Family-friendly home rentals with a hot tub
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Home in Newfane
4.98 out of 5 average rating, 120 reviewsPeaceful cabin close to skiing & Brattleboro
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Cabin in Londonderry
4.82 out of 5 average rating, 427 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
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Chalet in Dover
4.97 out of 5 average rating, 105 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
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Home in Dover
4.92 out of 5 average rating, 100 reviewsSpacious Cottage 5 mins to Mount Snow
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Home in Dover
4.98 out of 5 average rating, 126 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
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Home in Dover
4.97 out of 5 average rating, 75 reviewsWonderful House! Rec Room HotTub Firepit Garden!
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Home in Peru
4.63 out of 5 average rating, 57 reviewsNorman Rockwell Spacious Contemporary + Hot Tub
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Home in Halifax
4.87 out of 5 average rating, 45 reviewsRural VT Retreat—Complete Privacy on 140 Acres!
Family- and pet-friendly home rentals
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Chalet in Dover
4.93 out of 5 average rating, 272 reviewsA charming VT chalet
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Home in Newfane
4.95 out of 5 average rating, 172 reviewsAdorable home in Newfane
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Cabin in Brattleboro
4.89 out of 5 average rating, 461 reviewsCottage
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Farm stay in Marlboro
4.89 out of 5 average rating, 587 reviewsCarriage Barn - Marlboro
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Home in Weston
4.95 out of 5 average rating, 237 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
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Home in Dummerston
4.99 out of 5 average rating, 326 reviewsPinecone Pond
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Home in Guilford
4.93 out of 5 average rating, 183 reviewsPeaceful Country Home
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Cabin in Jamaica
4.87 out of 5 average rating, 273 reviewsGreen Mountain Modern House: iconic modern getaway
Family-friendly home rentals with a pool
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Home in Wilmington
4.9 out of 5 average rating, 135 reviews4 bedroom Ski House 15 min to Mount Snow
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Townhouse in Dover
4.96 out of 5 average rating, 140 reviewsBear's Den - Mt Snow Townhome w/ Heated Pool!
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Home in Wilmington
4.82 out of 5 average rating, 159 reviewsThe Vermont Barn (Mount Snow)
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Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
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Townhouse in Dover
4.93 out of 5 average rating, 72 reviewsCozy Bear- 1 mile to Mt Snow Ski Home
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Home in West Dover
5 out of 5 average rating, 43 reviewsThe Manor-Stunning Modern Farmhouse with Hot Tub
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Home in Dover
4.89 out of 5 average rating, 47 reviewsQueen Suite, Living Room, 2 TVs -Spring House 2
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Chalet in Wilmington
4.94 out of 5 average rating, 90 reviewsRustic Sunny Vermont Home near Mount Snow
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