Family-friendly holiday 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.
Holiday 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
Cabin in Monterey
Amazing Berkshire Mountains Cabin
Cabin in Saugerties
Container Cabin in the Catskills (Field)
Bungalow in Easthampton
The Creation Station
Home in Ancramdale
Ski & unwind in the country, stargaze in hot tub
Home in Craryville
Modern Home in Woods w/ Hot Tub 10 Miles to Hudson
Home in Craryville
The City Farmers Upstate. Farm house with hot tub
Home in Round Top
Escape in the Catskills w/hottub
Home in Hudson
Livingston Farmhouse Escape with hot tub and sauna
Family- and pet-friendly home rentals
Home in West Stockbridge
Peaceful Stockbridge Cabin in the Woods
Cabin in Lee
Spring sale! Cabin with views in the Berkshires
Cottage in Craryville
Columbia County Getaway - Raspberry Ridge Cottage
Cottage in Claverack
‘Clavashack’ Country Cottage
Farm stay in Kinderhook
Barn House: isolated sheep farm Hudson area
Rental unit in Sandisfield
Sunny Berkshire Studio Apartment
Yurt in Pattersonville
Mariaville Goat Farm Yurt
Rental unit in Great Barrington
Secluded but not isolated Berkshire Retreat
Family-friendly home rentals with a pool
Home in Ghent
Modern Barn on 12 acres w Sauna, FirePit+swimming
Guest house in Williamstown
Perfect Base for Your Berkshire Adventure
Home in Hudson
Casa Luna Country Retreat with Pool, Hudson, NY
Home in New Paltz
midcentury modern in ground pool walk 2 trail/town
Cabin in Saugerties
Lovely cabin by the stream
Rental unit in Rexford
Need a Getaway??
Rental unit in Earlton
Sweet Farm Stay
Home in Saugerties
Upstate Modern Scandinavian Barn in the Catskills
Quick stats about holiday 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
€ 101 before taxes and fees
Destinations to explore
- New City Holiday rentals
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