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
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
14–21 Oct
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
5–12 Aug
Cabin in Saugerties
4.86 out of 5 average rating, 172 reviewsContainer Cabin in the Catskills (Field)
29 Aug – 5 Sept
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
21–28 Jul
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
11–18 Jun
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
3–10 Oct
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
3–10 Mar
Cottage in Phoenicia
4.89 out of 5 average rating, 801 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
27 Jul – 3 Aug
Family- and pet-friendly home rentals
Flat in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
21–28 Oct
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
16–23 May
Guest house in Stephentown
5.0 out of 5 average rating, 361 reviewsDog Friendly Studio
25 Jan – 1 Feb
Flat in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
30 Mar – 6 Apr
Yurt in Pattersonville
4.99 out of 5 average rating, 778 reviewsMariaville Goat Farm Yurt
21–28 Apr
Home in New Paltz
4.97 out of 5 average rating, 680 reviewsVictorian Haven
19–26 Apr
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
2–9 Oct
Farm stay in West Simsbury
4.95 out of 5 average rating, 432 reviewsFlamig Farm Staycation
16–23 Nov
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
8–15 Dec
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
17–24 Jun
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
22–29 Sept
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
4–11 Oct
Home in New Paltz
4.98 out of 5 average rating, 436 reviewsmidcentury modern in ground pool walk 2 trail/town
14–21 Jul
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
29 Dec – 5 Jan
Townhouse in Hunter
4.91 out of 5 average rating, 136 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
22–29 May
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
14–21 Apr
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
£88 before taxes and fees
Destinations to explore
- New City Holiday rentals
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