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, 312 reviewsRiverfront Getaway
Oct 14 – 21
Cabin in Saugerties
4.86 out of 5 average rating, 173 reviewsContainer Cabin in the Catskills (Field)
Mar 16 – 23
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 5 – 12
Bungalow in Easthampton
4.92 out of 5 average rating, 433 reviewsThe Creation Station
Jul 23 – 30
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 7 – 14
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
Jun 11 – 18
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Mar 13 – 20
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Family- and pet-friendly home rentals
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Oct 23 – 30
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
Aug 18 – 23
Guesthouse in Stephentown
5.0 out of 5 average rating, 361 reviewsDog Friendly Studio
Feb 24 – Mar 3
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
Nov 26 – Dec 3
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Feb 17 – 24
Guest suite in Montague
4.93 out of 5 average rating, 164 reviewsGreat Falls Private Suite
Oct 13 – 20
Yurt in Pattersonville
4.99 out of 5 average rating, 778 reviewsMariaville Goat Farm Yurt
Dec 19 – 26
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 582 reviewsMagic Forest Farm's Mountain View Suite
Oct 19 – 26
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
Mar 22 – 29
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 30 – Sep 6
Townhouse in Hunter
4.91 out of 5 average rating, 136 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
May 14 – 21
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Oct 6 – 13
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
Sep 21 – 28
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Oct 8 – 15
Townhouse in Hudson
4.94 out of 5 average rating, 194 reviewsPalazzo Hudson: Luxury Pool, Hot Tub, and Sauna
Mar 22 – 29
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
Destinations to explore
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