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, 314 reviewsRiverfront Getaway
Cabin in Saugerties
4.86 out of 5 average rating, 176 reviewsContainer Cabin in the Catskills (Field)
Cottage in Shaftsbury
4.99 out of 5 average rating, 605 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
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, 252 reviewsAmazing Berkshire Mountains Cabin
Home in Highland
4.96 out of 5 average rating, 111 reviewsHouse in Highland: Secluded Retreat
Home in Craryville
4.98 out of 5 average rating, 190 reviewsModern Home in Woods w/ Hot Tub 10 Miles to Hudson
Cabin in Johnstown
4.9 out of 5 average rating, 321 reviewsMoose Cabin: Superior Quality Camp Garoga. HOT TUB
Family- and pet-friendly home rentals
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Farm stay in Kinderhook
4.86 out of 5 average rating, 207 reviewsBarn House: isolated sheep farm Hudson area
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 585 reviewsMagic Forest Farm's Mountain View Suite
Home in Ghent
4.87 out of 5 average rating, 272 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in New Paltz
4.97 out of 5 average rating, 683 reviewsVictorian Haven
Cabin in Jefferson
5.0 out of 5 average rating, 435 reviews"Far from the Madding Crowd" Cozy Cabin Retreat
Cottage in Claverack
4.98 out of 5 average rating, 247 reviews‘Clavashack’ Country Cottage
Family-friendly home rentals with a pool
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Bungalow in Easthampton
4.92 out of 5 average rating, 437 reviewsThe Creation Station
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Home in New Paltz
4.98 out of 5 average rating, 440 reviewsmidcentury modern in ground pool walk 2 trail/town
Barn in Bethel
4.98 out of 5 average rating, 204 reviewsEscape to a Restored New England Antique Milk Barn
Home in Cheshire
5.0 out of 5 average rating, 119 reviewsPool House
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