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
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Quick stats about holiday rentals in Great Barrington
Total rentals | 240 properties |
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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 |
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