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
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
Guesthouse 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 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
- New City Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Catskill Vacation rentals
- Albany Vacation rentals
- Catskill Mountains Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals New York
- Family-friendly rentals Massachusetts
- Family-friendly rentals Massachusetts
- Rentals with a washer and dryer Stockbridge
- Rentals with a patio Stockbridge
- House rentals Stockbridge
- Rentals with outdoor seating Stockbridge
- Rentals with a fireplace Stockbridge
- Rentals with pools Stockbridge
- Monthly Rentals Stockbridge
- Rentals with lake access Stockbridge
- Pet-friendly rentals Stockbridge
- Kid-friendly rentals Stockbridge
- Rentals with a fire pit Stockbridge
- Hotel rentals Stockbridge
- Rentals with breakfast Stockbridge
- Family-friendly rentals Berkshire County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom