Family-friendly vacation rentals in West Stockbridge
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in West 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 West 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 Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 5 – 12
Cabin in Saugerties
4.86 out of 5 average rating, 173 reviewsContainer Cabin in the Catskills (Field)
Jan 19 – 26
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Mar 13 – 20
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Apr 21 – 28
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
Jun 11 – 18
Home in Hudson
4.84 out of 5 average rating, 222 reviewsHudson Country Cottage, Fireplace, Pond, Hot Tub
Oct 23 – 30
Home in Ancramdale
4.93 out of 5 average rating, 127 reviewsSki & unwind in the country, stargaze in hot tub
Sep 21 – 28
Family- and pet-friendly home rentals
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
Sep 24 – Oct 1
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
Aug 18 – 23
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Feb 17 – 24
Home in Ghent
4.9 out of 5 average rating, 258 reviewsRenovated guesthouse on 52 acres!
Sep 8 – 15
Home in Chatham
4.93 out of 5 average rating, 187 reviewsBeautiful Lake/Mountain Views. Bright Sunlit Home.
Apr 15 – 22
Home in New Paltz
4.97 out of 5 average rating, 680 reviewsVictorian Haven
Apr 3 – 10
Yurt in Pattersonville
4.99 out of 5 average rating, 778 reviewsMariaville Goat Farm Yurt
Dec 19 – 26
Farm stay in West Simsbury
4.95 out of 5 average rating, 434 reviewsFlamig Farm Staycation
Feb 20 – 27
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
Jan 27 – Feb 3
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
Apartment in Earlton
4.93 out of 5 average rating, 279 reviewsSweet Farm Stay
Apr 5 – 12
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Oct 11 – 18
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
Sep 21 – 28
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep 10 – 17
Quick stats about vacation rentals that are family-friendly in West Stockbridge
Total rentals
50 properties
Wifi availability
50 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
1.6K reviews
Nightly prices starting at
G$27,147 GYD before taxes and fees
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