Family-friendly vacation rentals in Great Barrington
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Great Barrington
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 Great Barrington family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 314 reviewsRiverfront Getaway
Cabin in Monterey
4.95 out of 5 average rating, 252 reviewsAmazing Berkshire Mountains Cabin
Cabin in Saugerties
4.86 out of 5 average rating, 176 reviewsContainer Cabin in the Catskills (Field)
Home in Colebrook
4.99 out of 5 average rating, 204 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Home in Craryville
4.98 out of 5 average rating, 191 reviewsModern Home in Woods w/ Hot Tub 10 Miles to Hudson
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Home in Hudson
4.95 out of 5 average rating, 251 reviewsLivingston Farmhouse Escape with hot tub and sauna
Home in Ancramdale
4.93 out of 5 average rating, 127 reviewsSki & unwind in the country, stargaze in hot tub
Family- and pet-friendly home rentals
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
Cottage in Claverack
4.98 out of 5 average rating, 247 reviews‘Clavashack’ Country Cottage
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Loft in East Nassau
4.99 out of 5 average rating, 154 reviewsDog Friendly Farm Spring bird watching
Cabin in Red Hook
4.96 out of 5 average rating, 308 reviewsModern Upstate Cabin, near Rhinebeck NY
Farm stay in Kinderhook
4.86 out of 5 average rating, 207 reviewsBarn House: isolated sheep farm Hudson area
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 585 reviewsMagic Forest Farm's Mountain View Suite
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 272 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Home in New Paltz
4.98 out of 5 average rating, 440 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Townhouse in Hunter
4.91 out of 5 average rating, 136 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio & Pool w/Deck Mountain Views
Quick stats about vacation rentals that are family-friendly in Great Barrington
Total rentals
180 properties
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
90 properties allow pets
Total number of reviews
5.4K reviews
Nightly prices starting at
$70 before taxes and fees
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