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, 312 reviewsRiverfront Getaway
Dec 8 – 15
Cabin in Saugerties
4.86 out of 5 average rating, 173 reviewsContainer Cabin in the Catskills (Field)
Sep 30 – Oct 7
Cottage in Shaftsbury
4.99 out of 5 average rating, 601 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Apr 27 – May 4
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 2 – 9
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 6 – 13
Home in Woodstock
4.94 out of 5 average rating, 883 reviews1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole
Sep 12 – 19
Cabin in Johnstown
4.9 out of 5 average rating, 321 reviewsMoose Cabin: Superior Quality Camp Garoga. HOT TUB
Mar 26 – Apr 2
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Dec 14 – 21
Family- and pet-friendly home rentals
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
May 12 – 19
Yurt in Pattersonville
4.99 out of 5 average rating, 778 reviewsMariaville Goat Farm Yurt
Oct 19 – 26
Farm stay in West Simsbury
4.95 out of 5 average rating, 434 reviewsFlamig Farm Staycation
Feb 20 – 27
Cottage in Red Hook
4.98 out of 5 average rating, 599 reviewsbright serene + spacious barn
Sep 11 – 18
Cottage in Claverack
4.98 out of 5 average rating, 245 reviews‘Clavashack’ Country Cottage
Aug 18 – 23
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 583 reviewsMagic Forest Farm's Mountain View Suite
Aug 31 – Sep 7
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Oct 24 – 31
Tiny home in Jamaica
4.94 out of 5 average rating, 1146 reviewsApple Blossom Cottage: A Tiny House
Apr 4 – 11
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
Jan 27 – Feb 3
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 31 – Sep 7
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Nov 10 – 17
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Litchfield
4.93 out of 5 average rating, 164 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 4 – 11
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Oct 7 – 14
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
Jun 3 – 10
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Dec 28 – Jan 4
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