Family-friendly vacation rentals in Windham
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windham
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham family-friendly rentals
Family-friendly home rentals with a hot tub
Cabin in Londonderry
4.82 out of 5 average rating, 425 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
Cottage in Shaftsbury
4.99 out of 5 average rating, 611 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Home in Newfane
4.97 out of 5 average rating, 116 reviewsPeaceful cabin close to skiing & Brattleboro
Loft in Ludlow
4.95 out of 5 average rating, 739 reviewsSpacious Renovated Barn Apt on 100 acres!
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
Home in Colrain
4.94 out of 5 average rating, 159 reviewsSecluded Farmhouse Retreat - stunning views
Chalet in Dover
4.97 out of 5 average rating, 104 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Family- and pet-friendly home rentals
Home in Town of Rockingham
4.89 out of 5 average rating, 113 reviewsBeautiful Home in the Mountains - The Fox & Owl
Chalet in Dover
4.93 out of 5 average rating, 268 reviewsA charming VT chalet
Home in Grafton
4.97 out of 5 average rating, 133 reviewsEphriam Bruce House- ON RIVER IN VILLAGE CENTER
Guesthouse in Granville
4.9 out of 5 average rating, 799 reviewsMoon Valley Country Retreat no clean fee pets yes
Rental unit in Springfield
4.91 out of 5 average rating, 226 reviewsFarm Barn apt. 3 bedr, 2 bath, fiberoptic internet
Cottage in Dover
4.95 out of 5 average rating, 218 reviewsCozy summer cottage in the woods of southern VT
Chalet in Town of Rockingham
4.97 out of 5 average rating, 115 reviewsFantastic Mountain Views, Vermont
Cabin in Jamaica
4.87 out of 5 average rating, 268 reviewsGreen Mountain Modern House: iconic modern getaway
Family-friendly home rentals with a pool
Condo in Killington
4.92 out of 5 average rating, 394 reviewsBike Golf Hike Pico 1 bedroom 1 night Ok shuttle
Guesthouse in Williamstown
4.93 out of 5 average rating, 220 reviewsPerfect Base for Your Berkshire Adventure
Townhouse in Dover
4.96 out of 5 average rating, 137 reviewsBear's Den - Mt Snow Townhome w/ Heated Pool!
Home in Wilmington
4.9 out of 5 average rating, 133 reviews4 bedroom Ski House 15 min to Mount Snow
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
Condo in Killington
4.9 out of 5 average rating, 232 reviewsA Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Quick stats about vacation rentals that are family-friendly in Windham
Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1.4K reviews
Nightly prices starting at
$110 before taxes and fees
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