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.

Guest favorite
Loft in Great Barrington
The Old Red Barn
Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.
Apr 3 – 10
$139 per night
4.99 out of 5 average rating, 293 reviews
Guest favorite
Guest suite in South Lee
Sunny Riverside Apartment
The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.
Dec 7 – 14
$112 per night
4.92 out of 5 average rating, 188 reviews
Guest favorite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!
May 15 – 22
$79 per night
4.98 out of 5 average rating, 229 reviews

Popular amenities for West Stockbridge family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
Jun 8 – 15
$313 per night
4.95 out of 5 average rating, 247 reviews
Guest favorite
Home in Chester
Riverfront Getaway
Sep 5 – 12
$159 per night
4.96 out of 5 average rating, 305 reviews
Guest favorite
Cabin in Becket
Waldtreff - quiet grand cabin
May 22 – 29
$219 per night
5.0 out of 5 average rating, 253 reviews
Guest favorite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Feb 18 – 25
$198 per night
4.99 out of 5 average rating, 199 reviews
Guest favorite
Home in Craryville
The City Farmers Upstate. Farm house with hot tub
Sep 29 – Oct 6
$310 per night
4.93 out of 5 average rating, 216 reviews
Guest favorite
Home in Hudson
Hudson Country Cottage, Fireplace, Pond, Hot Tub
Feb 8 – 15
$328 per night
4.84 out of 5 average rating, 220 reviews
Guest favorite
Home in Hudson
Livingston Farmhouse Escape with hot tub and sauna
Apr 8 – 15
$458 per night
4.95 out of 5 average rating, 245 reviews
Guest favorite
Home in Ancramdale
Ski & unwind in the country, stargaze in hot tub
Mar 11 – 18
$165 per night
4.93 out of 5 average rating, 126 reviews
Guest favorite
Home in Saugerties
Upstate Modern Scandinavian Barn in the Catskills
Mar 29 – Apr 5
$598 per night
5.0 out of 5 average rating, 129 reviews
Guest favorite
Home in Craryville
Modern Home in Woods | Hot Tub | 20 mins to Skiing
Aug 18 – 25
$401 per night
4.98 out of 5 average rating, 182 reviews
Guest favorite
Home in Pittsfield
Beautiful House By The Lake W/Jetted Hot Tub
Apr 30 – May 7
$389 per night
4.83 out of 5 average rating, 161 reviews
Guest favorite
Cabin in Colebrook
Adorable, storybook log cabin
Aug 9 – 16
$185 per night
4.94 out of 5 average rating, 195 reviews

Family- and pet-friendly home rentals

Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Mar 15 – 22
$60 per night
4.83 out of 5 average rating, 151 reviews
Guest favorite
Home in Great Barrington
Your own private Berkshires retreat
Nov 17 – 24
$262 per night
4.9 out of 5 average rating, 111 reviews
Guest favorite
Guesthouse in Stephentown
Dog Friendly Studio
Nov 1 – 8
$167 per night
5.0 out of 5 average rating, 352 reviews
Superhost
Cottage in Canaan
Plan your Berkshires by the lake
Apr 1 – 8
$194 per night
4.9 out of 5 average rating, 125 reviews
Guest favorite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home.
Feb 17 – 24
$300 per night
4.93 out of 5 average rating, 187 reviews
Guest favorite
Apartment in Great Barrington
Secluded but not isolated Berkshire Retreat
Aug 13 – 20
$177 per night
4.93 out of 5 average rating, 177 reviews
Guest favorite
Cottage in Claverack
‘Clavashack’ Country Cottage
Jun 29 – Jul 6
$162 per night
4.98 out of 5 average rating, 241 reviews
Superhost
Home in Ghent
Renovated guesthouse on 52 acres!
Oct 11 – 18
$203 per night
4.9 out of 5 average rating, 255 reviews
Guest favorite
Cabin in Hillsdale
Tory Hill Cabin; (North Mountain Cottages)
Jul 20 – 27
$152 per night
4.9 out of 5 average rating, 168 reviews
Guest favorite
Cottage in Craryville
Columbia County Getaway - Raspberry Ridge Cottage
Feb 14 – 21
$158 per night
4.91 out of 5 average rating, 467 reviews
Superhost
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
Aug 16 – 23
$527 per night
4.81 out of 5 average rating, 243 reviews
Guest favorite
Cottage in Red Hook
bright serene + spacious barn
Jul 31 – Aug 7
$280 per night
4.98 out of 5 average rating, 586 reviews

Family-friendly home rentals with a pool

Guest favorite
Home in Ghent
Modern Barn on 12 acres w Sauna, FirePit+swimming
May 16 – 23
$237 per night
4.87 out of 5 average rating, 259 reviews
Guest favorite
Cabin in Red Hook
Modern Upstate Cabin, near Rhinebeck NY
Aug 14 – 21
$405 per night
4.96 out of 5 average rating, 300 reviews
Guest favorite
Home in Sheffield
Race Mountain House
Aug 14 – 21
$483 per night
4.85 out of 5 average rating, 114 reviews
Guest favorite
Guesthouse in Williamstown
Perfect Base for Your Berkshire Adventure
Aug 8 – 15
$146 per night
4.93 out of 5 average rating, 219 reviews
Guest favorite
Barn in Saugerties
Barn on the Pond Barn Style Lodging
Apr 19 – 26
$975 per night
4.97 out of 5 average rating, 105 reviews
Guest favorite
Bungalow in Williamstown
Hollywood Bungalow in the Berkshires
Dec 13 – 20
$204 per night
4.89 out of 5 average rating, 201 reviews
Guest favorite
Apartment in Earlton
Sweet Farm Stay
Apr 3 – 10
$250 per night
4.93 out of 5 average rating, 279 reviews
Guest favorite
Guesthouse in Woodstock
Light-filled Cabin on 10 acres with pool & sauna
Apr 4 – 9
$187 per night
4.94 out of 5 average rating, 214 reviews
Guest favorite
Farm stay in Rhinebeck
Historical property, unique kitchen, Rhinebeck
Nov 1 – 8
$821 per night
4.94 out of 5 average rating, 169 reviews
Superhost
Home in Saugerties
Hillside Escape: HIT's Home w/ Pool & Hot Tub
Feb 9 – 16
$256 per night
4.81 out of 5 average rating, 123 reviews
Guest favorite
Home in Woodstock
Woodstock Modern Gem, Glorious Heated Saline Pool
Mar 17 – 24
$410 per night
4.96 out of 5 average rating, 107 reviews
Guest favorite
Home in Catskill
Daydream Mountain Art-Chateau '73 | I ❤️ Catskill
Apr 25 – May 2
$570 per night
4.95 out of 5 average rating, 174 reviews

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

$120 before taxes and fees

Destinations to explore