Family-friendly vacation rentals in The Berkshires
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in The Berkshires
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 The Berkshires family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 313 reviewsRiverfront Getaway
Cottage in Shaftsbury
4.99 out of 5 average rating, 605 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Cabin in Saugerties
4.86 out of 5 average rating, 175 reviewsContainer Cabin in the Catskills (Field)
Home in Highland
4.96 out of 5 average rating, 111 reviewsHouse in Highland: Secluded Retreat
Home in Colebrook
4.99 out of 5 average rating, 204 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Cabin in Johnstown
4.9 out of 5 average rating, 321 reviewsMoose Cabin: Superior Quality Camp Garoga. HOT TUB
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Family- and pet-friendly home rentals
Farm stay in Kinderhook
4.86 out of 5 average rating, 207 reviewsBarn House: isolated sheep farm Hudson area
Cottage in Craryville
4.91 out of 5 average rating, 483 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Yurt in Pattersonville
4.99 out of 5 average rating, 784 reviewsMariaville Goat Farm Yurt
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 584 reviewsMagic Forest Farm's Mountain View Suite
Home in New Paltz
4.97 out of 5 average rating, 681 reviewsVictorian Haven
Cottage in Red Hook
4.98 out of 5 average rating, 600 reviewsbright serene + spacious barn
Cottage in Claverack
4.98 out of 5 average rating, 247 reviews‘Clavashack’ Country Cottage
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in New Paltz
4.98 out of 5 average rating, 439 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Saugerties
5.0 out of 5 average rating, 133 reviewsUpstate Modern Scandinavian Barn in the Catskills
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