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
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
7–14 Dec
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
5–12 Jun
Cabin in Saugerties
4.86 out of 5 average rating, 172 reviewsContainer Cabin in the Catskills (Field)
25 Jan – 1 Feb
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
2–9 Apr
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
21–26 Jul
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
20–27 Mar
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
15–22 May
Home in Highland
4.96 out of 5 average rating, 107 reviewsHouse in Highland: Secluded Retreat
22 Feb – 1 Mar
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
1–8 Jan
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
1–8 Nov
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
2–9 Jun
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
11–18 May
Home in New Paltz
4.97 out of 5 average rating, 678 reviewsVictorian Haven
8–15 Jan
Loft in East Nassau
4.99 out of 5 average rating, 154 reviewsDog Friendly Farm Spring bird watching
21–28 Jul
Cottage in Red Hook
4.98 out of 5 average rating, 598 reviewsbright serene + spacious barn
14–21 Nov
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
11–18 Jul
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
4–11 Dec
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
21–28 Sep
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
7–14 May
Townhouse in Hunter
4.91 out of 5 average rating, 136 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
6–13 May
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
10–17 Sep
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
18–25 Oct
Home in New Paltz
4.98 out of 5 average rating, 436 reviewsmidcentury modern in ground pool walk 2 trail/town
6–13 Sep
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
31 Oct – 7 Nov
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
$118 NZD before taxes and fees
Destinations to explore
- New City Holiday rentals
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