Family-friendly holiday 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.
Holiday 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
Home in Newfane
4.97 out of 5 average rating, 115 reviewsPeaceful cabin close to skiing & Brattleboro
12–19 Apr
Cabin in Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
23–30 Aug
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
16–23 Sep
Chalet in Dover
4.97 out of 5 average rating, 104 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
18–25 Dec
Home in Jamaica
4.96 out of 5 average rating, 47 reviews4 Bedroom on 90 Acres in the mountains of Vermont!
22–29 Apr
Home in Dover
4.97 out of 5 average rating, 75 reviewsWonderful House! Rec Room HotTub Firepit Garden!
25 Sep – 2 Oct
Home in Dover
4.93 out of 5 average rating, 98 reviewsSpacious Cottage 5 mins to Mount Snow
7–14 Mar
Home in Peru
4.63 out of 5 average rating, 56 reviewsNorman Rockwell Spacious Contemporary + Hot Tub
15–22 Dec
Family- and pet-friendly home rentals
Loft in Wilmington
4.92 out of 5 average rating, 172 reviewsWalk to Village/Lake Whitingham
15–22 Jun
Farm stay in Marlboro
4.89 out of 5 average rating, 577 reviewsCarriage Barn - Marlboro
22–29 Oct
Tiny home in Jamaica
4.94 out of 5 average rating, 1145 reviewsApple Blossom Cottage: A Tiny House
9–16 Jun
Guest house in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
19–26 Aug
Home in Guilford
4.94 out of 5 average rating, 173 reviewsPeaceful Country Home
3–10 Apr
Home in Dummerston
4.99 out of 5 average rating, 323 reviewsPinecone Pond
20–27 Jan
Cabin in Jamaica
4.88 out of 5 average rating, 265 reviewsGreen Mountain Modern House: iconic modern getaway
13–20 Mar
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
13–20 Sep
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
5–12 Sep
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
20–27 Nov
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
30 Jan – 6 Feb
Apartment in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
14–21 Oct
Townhouse in Dover
4.93 out of 5 average rating, 71 reviewsCozy Bear- 1 mile to Mt Snow Ski Home
3–10 Jun
Home in Londonderry
4.83 out of 5 average rating, 53 reviewsDeer Hill, With a Pool and Central HVAC system
26 Oct – 2 Nov
Home in West Dover
5.0 out of 5 average rating, 42 reviewsThe Manor-Stunning Modern Farmhouse with Hot Tub
6–13 Nov
Home in Dover
4.94 out of 5 average rating, 31 reviewsLuxury King Suite, fireplace, bunkbed- Farmhouse 4
19–24 May
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Boston
- Family-friendly rentals Vermont
- Family-friendly rentals New York
- Family-friendly rentals New Hampshire
- Cabin rentals Windham County
- Rentals with a patio Windham County
- Rentals with lake access Windham County
- Monthly Rentals Windham County
- Bed and breakfasts Windham County
- Tiny house rentals Windham County
- Rentals with outdoor seating Windham County
- Townhouse rentals Windham County
- Pet-friendly rentals Windham County
- Rentals with a fireplace Windham County
- Family-friendly rentals Windham County
- Rentals with beach access Windham County
- House rentals Windham County
- Rentals with pools Windham County
- Waterfront rentals Windham County
- Farm stay rentals Windham County
- Rentals with breakfast Windham County
- Beachfront rentals Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with an accessible-height toilet Windham County
- Rentals with a washing machine and dryer Windham County
- Private suite rentals Windham County
- Apartment rentals Windham County
- Rentals with a sauna Windham County
- Chalet rentals Windham County
- Rentals with a kayak Windham County
- Rentals with a hot tub Windham County
- Guest house rentals Windham County
- Rentals with an EV charger Windham County
- Fitness-friendly rentals Windham County
- Flat rentals Windham County
- Rentals with a firepit Windham County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom