Vacation rentals in Great Barrington

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Top-rated holiday rentals in Great Barrington

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Loft in Great Barrington
The Old Red Barn
Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.
22–29 Apr
$325 NZD per night
4.99 out of 5 average rating, 295 reviews
Guest favourite
Home in Lee
Cozy Berkshires Cottage
Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)
5–12 Sep
$267 NZD per night
4.89 out of 5 average rating, 234 reviews
Guest favourite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
29 Aug – 5 Sep
$216 NZD per night
4.93 out of 5 average rating, 247 reviews

Popular amenities for Great Barrington holiday rentals

Stay near Great Barrington's top sights

Ski Butternut218 locals recommend
Theory Wellness: Recreational and Medical Marijuana Dispensary MA10 locals recommend
Monument Mountain Reservation112 locals recommend
Xicohtencatl Restaurant52 locals recommend
GB Eats32 locals recommend
The Bistro Box47 locals recommend

Other great holiday rentals in Great Barrington

Guest favourite
Bungalow in Hillsdale
Copake Lake & Catamount/Berkshires Cottage
20–27 Apr
$201 NZD per night
4.86 out of 5 average rating, 129 reviews
Guest favourite
Cottage in Hillsdale
Cozy Cottage Catamount, Berkshires Walk to Brewery
11–18 Jul
$238 NZD per night
4.94 out of 5 average rating, 171 reviews
Guest favourite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
30 Nov – 7 Dec
$845 NZD per night
4.96 out of 5 average rating, 136 reviews
Guest favourite
Home in Egremont
A sunny, quiet chalet beautifully decorated.
10–17 Aug
$923 NZD per night
4.97 out of 5 average rating, 113 reviews
Guest favourite
Guest suite in Great Barrington
Sweet 1-bedroom with salt water pool
19–26 May
$309 NZD per night
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Great Barrington
Quiet home on the hill.
5–12 Sep
$315 NZD per night
4.93 out of 5 average rating, 67 reviews
Guest favourite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
3–10 Dec
$401 NZD per night
5.0 out of 5 average rating, 44 reviews
Guest favourite
Guesthouse in Great Barrington
Studio in Bucolic Berkshire Setting
13–20 Apr
$251 NZD per night
4.97 out of 5 average rating, 90 reviews
Guest favourite
Apartment in Great Barrington
Lush Setting, Private Deck, Queen Bed in GB
20–27 Dec
$218 NZD per night
4.86 out of 5 average rating, 64 reviews
Guest favourite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
26 Nov – 3 Dec
$977 NZD per night
4.94 out of 5 average rating, 53 reviews
Guest favourite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
10–17 Sep
$1,090 NZD per night
4.97 out of 5 average rating, 30 reviews
Guest favourite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
6–13 Dec
$970 NZD per night
5.0 out of 5 average rating, 59 reviews

Quick stats about holiday rentals in Great Barrington

Total rentals

240 properties

Rentals with dedicated workspaces

130 properties have a dedicated workspace

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

120 properties allow pets

Family-friendly rentals

170 properties are a good fit for families

Total number of reviews

8.1K reviews

Destinations to explore