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
Mar 20 – 27
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Feb 24 – Mar 3
Home in Highland
4.96 out of 5 average rating, 108 reviewsHouse in Highland: Secluded Retreat
Jan 31 – Feb 7
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 26 – Sep 2
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
May 28 – Jun 4
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
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Dec 25 – Jan 1
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 22 – 29
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
May 13 – 20
Cottage in Claverack
4.98 out of 5 average rating, 245 reviews‘Clavashack’ Country Cottage
Aug 18 – 23
Yurt in Pattersonville
4.99 out of 5 average rating, 778 reviewsMariaville Goat Farm Yurt
Apr 15 – 22
Farm stay in West Simsbury
4.95 out of 5 average rating, 434 reviewsFlamig Farm Staycation
Nov 26 – Dec 3
Cottage in Red Hook
4.98 out of 5 average rating, 599 reviewsbright serene + spacious barn
Nov 5 – 12
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Oct 25 – Nov 1
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 1 – 8
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Oct 14 – 21
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, 165 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 4 – 11
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 7 – 14
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Oct 8 – 15
Barn in Bethel
4.98 out of 5 average rating, 203 reviewsEscape to a Restored New England Antique Milk Barn
Feb 6 – 13
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