Family-friendly vacation rentals in Windham County
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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 Newfane
4.97 out of 5 average rating, 115 reviewsPeaceful cabin close to skiing & Brattleboro
Apr 13 – 20
Cabin in Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
Aug 25 – Sep 1
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
Nov 15 – 22
Chalet in Dover
4.97 out of 5 average rating, 104 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Dec 19 – 26
Home in Jamaica
4.96 out of 5 average rating, 47 reviews4 Bedroom on 90 Acres in the mountains of Vermont!
Apr 23 – 30
Home in Dover
4.97 out of 5 average rating, 75 reviewsWonderful House! Rec Room HotTub Firepit Garden!
Aug 13 – 20
Home in Peru
4.63 out of 5 average rating, 56 reviewsNorman Rockwell Spacious Contemporary + Hot Tub
Dec 16 – 23
Home in Dover
4.93 out of 5 average rating, 98 reviewsSpacious Cottage 5 mins to Mount Snow
Mar 8 – 15
Family- and pet-friendly home rentals
Cottage in Jamaica
4.82 out of 5 average rating, 466 reviewsForest Cottage ~ 7min to Stratton, Private, Views
Jun 18 – 25
Guesthouse in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
Jul 6 – 13
Loft in Wilmington
4.92 out of 5 average rating, 172 reviewsWalk to Village/Lake Whitingham
Oct 16 – 23
Farm stay in Marlboro
4.89 out of 5 average rating, 577 reviewsCarriage Barn - Marlboro
Oct 4 – 11
Home in Guilford
4.94 out of 5 average rating, 173 reviewsPeaceful Country Home
Feb 13 – 20
Home in Dummerston
4.99 out of 5 average rating, 323 reviewsPinecone Pond
Jan 20 – 27
Cabin in Jamaica
4.88 out of 5 average rating, 265 reviewsGreen Mountain Modern House: iconic modern getaway
Mar 13 – 20
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Sep 13 – 20
Family-friendly home rentals with a pool
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
Jan 16 – 23
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Nov 21 – 28
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Oct 15 – 22
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Jan 31 – Feb 7
Home in Londonderry
4.83 out of 5 average rating, 53 reviewsDeer Hill, With a Pool and Central HVAC system
Jul 15 – 22
Townhouse in Dover
4.93 out of 5 average rating, 71 reviewsCozy Bear- 1 mile to Mt Snow Ski Home
Sep 25 – Oct 2
Chalet in Wilmington
4.94 out of 5 average rating, 89 reviewsRustic Sunny Vermont Home near Mount Snow
Oct 14 – 21
Home in West Dover
5.0 out of 5 average rating, 42 reviewsThe Manor-Stunning Modern Farmhouse with Hot Tub
May 10 – 17
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