Family-friendly holiday 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.
Holiday 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
14–21 Oct
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
9–16 Oct
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
20–27 Aug
Home in Hudson
4.84 out of 5 average rating, 222 reviewsHudson Country Cottage, Fireplace, Pond, Hot Tub
13–20 Mar
Cabin in Saugerties
4.86 out of 5 average rating, 172 reviewsContainer Cabin in the Catskills (Field)
18–25 Oct
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
28 Oct – 4 Nov
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
22–29 Jun
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
24–31 Dec
Family- and pet-friendly home rentals
Home in Ghent
4.9 out of 5 average rating, 258 reviewsRenovated guesthouse on 52 acres!
5–12 Sep
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
20–27 Dec
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
24 Sep – 1 Oct
Home in Chatham
4.93 out of 5 average rating, 187 reviewsBeautiful Lake/Mountain Views. Bright Sunlit Home.
4–11 Feb
Farm stay in Kinderhook
4.85 out of 5 average rating, 205 reviewsBarn House: isolated sheep farm Hudson area
23–30 Mar
Yurt in Pattersonville
4.99 out of 5 average rating, 778 reviewsMariaville Goat Farm Yurt
21–28 Apr
Cottage in Red Hook
4.98 out of 5 average rating, 599 reviewsbright serene + spacious barn
7–14 Nov
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
23–30 Aug
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
23–30 Jan
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
16–23 Jun
Townhouse in Hunter
4.91 out of 5 average rating, 136 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
16–23 May
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
8–15 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
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
24 Nov – 1 Dec
Apartment in Earlton
4.93 out of 5 average rating, 279 reviewsSweet Farm Stay
12–19 Jan
Townhouse in Hudson
4.94 out of 5 average rating, 194 reviewsPalazzo Hudson: Luxury Pool, Hot Tub, and Sauna
17–24 Mar
Quick stats about holiday rentals that are family-friendly in West Stockbridge
Total rentals
50 properties
Wi-Fi availability
50 properties include access to Wi-Fi
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
$218 NZD before taxes and fees
Destinations to explore
- New City Holiday rentals
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- Rentals with a washing machine and dryer West Stockbridge
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