Family-friendly holiday 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.
Holiday 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
14–21 Apr
Cabin in Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
25 Aug – 1 Sep
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
17–24 Sep
Chalet in Dover
4.97 out of 5 average rating, 104 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
20–27 Dec
Home in Jamaica
4.96 out of 5 average rating, 47 reviews4 Bedroom on 90 Acres in the mountains of Vermont!
24 Apr – 1 May
Home in Dover
4.97 out of 5 average rating, 75 reviewsWonderful House! Rec Room HotTub Firepit Garden!
29 Sep – 6 Oct
Home in Dover
4.93 out of 5 average rating, 98 reviewsSpacious Cottage 5 mins to Mount Snow
9–16 Mar
Home in Peru
4.63 out of 5 average rating, 56 reviewsNorman Rockwell Spacious Contemporary + Hot Tub
17–24 Dec
Family- and pet-friendly home rentals
Loft in Wilmington
4.92 out of 5 average rating, 172 reviewsWalk to Village/Lake Whitingham
30 Jun – 7 Jul
Farm stay in Marlboro
4.89 out of 5 average rating, 577 reviewsCarriage Barn - Marlboro
23–30 Jun
Home in Dummerston
4.99 out of 5 average rating, 323 reviewsPinecone Pond
28 Feb – 7 Mar
Guesthouse in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
11–18 Feb
Home in Guilford
4.94 out of 5 average rating, 173 reviewsPeaceful Country Home
18–25 Dec
Cabin in Jamaica
4.88 out of 5 average rating, 265 reviewsGreen Mountain Modern House: iconic modern getaway
5–12 Sep
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
10–17 Sep
Chalet in Town of Rockingham
4.96 out of 5 average rating, 113 reviewsFantastic Mountain Views, Vermont
21–28 Jan
Family-friendly home rentals with a pool
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
1–8 Dec
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
22–29 Nov
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
31 Jan – 7 Feb
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
8–15 Feb
Home in Londonderry
4.83 out of 5 average rating, 53 reviewsDeer Hill, With a Pool and Central HVAC system
24–31 Jul
Home in West Dover
5.0 out of 5 average rating, 42 reviewsThe Manor-Stunning Modern Farmhouse with Hot Tub
16–23 Nov
Home in Dover
4.94 out of 5 average rating, 31 reviewsLuxury King Suite, fireplace, bunkbed- Farmhouse 4
19–24 May
Chalet in Wilmington
4.94 out of 5 average rating, 89 reviewsRustic Sunny Vermont Home near Mount Snow
15–22 Oct
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