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
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Sep 16 – 23
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 13 – 20
Cabin in Saugerties
4.86 out of 5 average rating, 172 reviewsContainer Cabin in the Catskills (Field)
Sep 27 – Oct 4
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
Jul 21 – 28
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Oct 6 – 13
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
Jul 7 – 14
Home in Ancramdale
4.93 out of 5 average rating, 127 reviewsSki & unwind in the country, stargaze in hot tub
Jun 4 – 11
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
Dec 17 – 24
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
Nov 8 – 15
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Mar 16 – 23
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
Jun 4 – 11
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
May 9 – 16
Loft in East Nassau
4.99 out of 5 average rating, 154 reviewsDog Friendly Farm Spring bird watching
Oct 20 – 27
Home in New Paltz
4.97 out of 5 average rating, 679 reviewsVictorian Haven
Mar 3 – 10
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Apr 10 – 17
Cottage in Red Hook
4.98 out of 5 average rating, 599 reviewsbright serene + spacious barn
Oct 29 – Nov 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
Mar 18 – 25
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Oct 15 – 22
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 10 – 17
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Aug 11 – 18
Home in New Paltz
4.98 out of 5 average rating, 436 reviewsmidcentury modern in ground pool walk 2 trail/town
Sep 6 – 13
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Sep 25 – Oct 2
Guest suite in New Paltz
4.95 out of 5 average rating, 327 reviewsMajestic Studio with Shawangunk Mountain Views
Aug 5 – 12
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Oct 17 – 24
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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