Family-friendly holiday 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.
Holiday 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
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, 177 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 Ancramdale
4.93 out of 5 average rating, 127 reviewsSki & unwind in the country, stargaze in hot tub
Home in Highland
4.96 out of 5 average rating, 111 reviewsHouse in Highland: Secluded Retreat
Home in Hudson
4.95 out of 5 average rating, 251 reviewsLivingston Farmhouse Escape with hot tub and sauna
Family- and pet-friendly home rentals
Flat 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
Guest house 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
Home in New Paltz
4.97 out of 5 average rating, 684 reviewsVictorian Haven
Home in Ghent
4.9 out of 5 average rating, 259 reviewsRenovated guesthouse on 52 acres!
Cottage in Red Hook
4.98 out of 5 average rating, 601 reviewsbright serene + spacious barn
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
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
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, 137 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Townhouse in Hudson
4.94 out of 5 average rating, 195 reviewsPalazzo Hudson: Luxury Pool, Hot Tub, and Sauna
Quick stats about holiday 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
€ 65 before taxes and fees
Destinations to explore
- New City Holiday rentals
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