Holiday 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.
25 Jun – 2 Jul
$199 SGD per night
4.99 out of 5 average rating, 295 reviews
Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon
13–20 Aug
$471 SGD per night
4.94 out of 5 average rating, 345 reviews
Guest favourite
Flat 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!
27 Aug – 3 Sep
$126 SGD 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
Home in New Marlborough
Lake House in the Berkshire (4min to Ski ButterNut
21–28 Apr
$268 SGD per night
4.89 out of 5 average rating, 122 reviews
Guest favourite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
22 Feb – 1 Mar
$255 SGD per night
5.0 out of 5 average rating, 44 reviews
Guest favourite
Guest suite in Great Barrington
Sweet 1-bedroom with salt water pool
14–21 May
$168 SGD 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
$199 SGD per night
4.93 out of 5 average rating, 67 reviews
Guest favourite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
4–11 May
$433 SGD per night
5.0 out of 5 average rating, 59 reviews
Guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
24 Apr – 1 May
$331 SGD per night
5.0 out of 5 average rating, 92 reviews
Guest favourite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
31 May – 7 Jun
$561 SGD per night
4.97 out of 5 average rating, 30 reviews
Guest favourite
Home in Great Barrington
Charming Cottage - Walk To Town
5–12 May
$287 SGD per night
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
21–28 Dec
$827 SGD per night
4.97 out of 5 average rating, 37 reviews
Guest favourite
Home in Great Barrington
Cozy charming home in the heart of the Berkshires!
9–16 Apr
$331 SGD per night
4.95 out of 5 average rating, 58 reviews
Guest favourite
Home in Great Barrington
Renovated Downtown Great Barrington House
28 May – 4 Jun
$541 SGD per night
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
21–28 Nov
$557 SGD per night
4.94 out of 5 average rating, 53 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