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, 311 reviewsRiverfront Getaway
Sep 6 – 13
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
Jun 5 – 12
Cabin in Saugerties
4.86 out of 5 average rating, 171 reviewsContainer Cabin in the Catskills (Field)
Dec 18 – 25
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Apr 1 – 8
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Oct 11 – 18
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
Jun 10 – 15
Home in Round Top
4.96 out of 5 average rating, 160 reviewsEscape in the Catskills w/hottub
May 16 – 23
Home in Craryville
4.98 out of 5 average rating, 187 reviewsModern Home in Woods | Hot Tub | 20 mins to Skiing
Sep 5 – 12
Family- and pet-friendly home rentals
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Dec 3 – 10
Cottage in Craryville
4.91 out of 5 average rating, 481 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Oct 30 – Nov 6
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
May 31 – Jun 7
Home in New Paltz
4.97 out of 5 average rating, 678 reviewsVictorian Haven
Feb 28 – Mar 7
Loft in East Nassau
4.99 out of 5 average rating, 153 reviewsDog Friendly Farm Spring bird watching
Aug 29 – Sep 5
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
Oct 3 – 10
Cottage in Red Hook
4.98 out of 5 average rating, 598 reviewsbright serene + spacious barn
Dec 6 – 13
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Mar 29 – Apr 5
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
Nov 12 – 19
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
May 3 – 10
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Jun 23 – 30
Home in New Paltz
4.98 out of 5 average rating, 435 reviewsmidcentury modern in ground pool walk 2 trail/town
Nov 26 – Dec 3
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 8 – 15
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Aug 3 – 10
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
May 16 – 23
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Oct 27 – Nov 3
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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