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 10 – 17
Cabin in Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
Aug 5 – 12
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
Jul 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 16 – 23
Home in Jamaica
4.96 out of 5 average rating, 47 reviews4 Bedroom on 90 Acres in the mountains of Vermont!
Apr 19 – 26
Home in Dover
4.97 out of 5 average rating, 75 reviewsWonderful House! Rec Room HotTub Firepit Garden!
Oct 12 – 19
Home in Dover
4.93 out of 5 average rating, 98 reviewsSpacious Cottage 5 mins to Mount Snow
Mar 5 – 12
Home in Peru
4.63 out of 5 average rating, 56 reviewsNorman Rockwell Spacious Contemporary + Hot Tub
Dec 13 – 20
Family- and pet-friendly home rentals
Loft in Wilmington
4.92 out of 5 average rating, 172 reviewsWalk to Village/Lake Whitingham
Jun 13 – 20
Home in Newfane
4.95 out of 5 average rating, 171 reviewsAdorable home in Newfane
Mar 31 – Apr 7
Farm stay in Marlboro
4.89 out of 5 average rating, 577 reviewsCarriage Barn - Marlboro
Dec 26 – Jan 2
Guesthouse in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
Apr 25 – May 2
Home in Guilford
4.94 out of 5 average rating, 173 reviewsPeaceful Country Home
Mar 25 – Apr 1
Home in Dummerston
4.99 out of 5 average rating, 323 reviewsPinecone Pond
Nov 8 – 15
Cabin in Jamaica
4.88 out of 5 average rating, 264 reviewsGreen Mountain Modern House: iconic modern getaway
Jan 20 – 27
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
Oct 16 – 23
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Nov 18 – 25
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Jan 27 – Feb 3
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Feb 4 – 11
Home in Londonderry
4.83 out of 5 average rating, 53 reviewsDeer Hill, With a Pool and Central HVAC system
Aug 28 – Sep 4
Townhouse in Dover
4.93 out of 5 average rating, 71 reviewsCozy Bear- 1 mile to Mt Snow Ski Home
Nov 21 – 28
Home in West Dover
5.0 out of 5 average rating, 42 reviewsThe Manor-Stunning Modern Farmhouse with Hot Tub
Nov 8 – 15
Chalet in Wilmington
4.94 out of 5 average rating, 89 reviewsRustic Sunny Vermont Home near Mount Snow
Oct 11 – 18
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