Family-friendly vacation rentals in Stockbridge
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Stockbridge
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 Stockbridge family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
Cabin in Saugerties
4.86 out of 5 average rating, 171 reviewsContainer Cabin in the Catskills (Field)
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Home in Round Top
4.96 out of 5 average rating, 160 reviewsEscape in the Catskills w/hottub
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
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Guesthouse in Stephentown
5.0 out of 5 average rating, 360 reviewsDog Friendly Studio
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
Home in New Paltz
4.97 out of 5 average rating, 678 reviewsVictorian Haven
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Townhouse in Hunter
4.91 out of 5 average rating, 136 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Home in New Paltz
4.98 out of 5 average rating, 435 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Quick stats about vacation rentals that are family-friendly in Stockbridge
Total rentals
80 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Total number of reviews
2.7K reviews
Nightly prices starting at
$110 before taxes and fees
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