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
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Popular amenities for Windham County family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Londonderry
4.94 out of 5 average rating, 67 reviewsSoLo House: 5BD, Spacious & Peaceful near Mtns
Cabin in Whitingham
4.98 out of 5 average rating, 58 reviewsVermont Log Cabin, Lake front. Close to Mount Snow
Chalet in Dover
4.97 out of 5 average rating, 107 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Home in Dover
4.96 out of 5 average rating, 26 reviewsPost & Beam house with Amazing views, Hot tub
Cabin in Londonderry
4.82 out of 5 average rating, 446 reviewsStunning Rustic Apple Barn - hot tub & sauna
Home in Newfane
4.98 out of 5 average rating, 130 reviewsPeaceful cabin close to skiing & Brattleboro
Home in Peru
4.63 out of 5 average rating, 57 reviewsNorman Rockwell Spacious Contemporary + Hot Tub
Rental unit in Londonderry
4.96 out of 5 average rating, 567 reviewsVermont Getaway Apartment
Family- and pet-friendly home rentals
Chalet in Readsboro
4.85 out of 5 average rating, 306 reviewsThe King's Cottage
Cabin in Brattleboro
4.88 out of 5 average rating, 484 reviewsCottage
Rental unit in Town of Rockingham
4.82 out of 5 average rating, 171 reviewsApartment on Main Street
Cabin in Jamaica
4.89 out of 5 average rating, 370 reviewsForest Cabin-Swim-Views-Fire Pit-7 min to Stratton
Home in Readsboro
4.86 out of 5 average rating, 124 reviewsRelax in Peaceful Vermont! (Pet Friendly)
Tiny home in Jamaica
4.94 out of 5 average rating, 1,211 reviewsApple Blossom Cottage: A Tiny House
Home in Wardsboro
4.94 out of 5 average rating, 148 reviewsSawmill Road - between Stratton and Mount Snow
Home in Jamaica
4.86 out of 5 average rating, 277 reviewsYellow Sweetie at the Base of Stratton
Family-friendly home rentals with a pool
Townhouse in Dover
4.96 out of 5 average rating, 143 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Chalet in Wilmington
4.95 out of 5 average rating, 92 reviewsRustic Sunny Vermont Home near Mount Snow
Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
Condo in Dover
4.87 out of 5 average rating, 228 reviewsMt Snow Ski In/Out at Seasons
Home in Newfane
4.92 out of 5 average rating, 48 reviews6 BR Perfect Private Retreat in Vermont!
Townhouse in West Dover
4.65 out of 5 average rating, 181 reviewsMOUNT SNOW CHALET/LOFT CONDO
Home in Dover
5 out of 5 average rating, 54 reviewsThe Villa - Industrial Farmhouse with Hot Tub
Townhouse in Dover
4.93 out of 5 average rating, 76 reviewsCozy Bear- 1 mile to Mt Snow Ski Home
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