Vacation rentals in Great Barrington

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Top-rated vacation rentals in Great Barrington

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

Guest favourite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

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.

Apr. 5 – 12

$272 CAD per night
Guest favourite

Home in Lee

4.89 out of 5 average rating, 234 reviews

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)

Sep. 13 – 20

$210 CAD per night
Guest favourite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

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!

Sep. 14 – 21

$179 CAD per night

Popular amenities for Great Barrington vacation 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 vacation rentals in Great Barrington

Guest favourite

Home in Egremont

4.93 out of 5 average rating, 254 reviews

Modern Farm House 5 minutes from Great Barrington

Jun. 21 – 28

$695 CAD per night
Guest favourite

Tiny homes in Chatham

4.99 out of 5 average rating, 178 reviews

Tiny House on 70 Private Acres in Hudson Valley

Sep. 13 – 20

$223 CAD per night
Guest favourite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 179 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Jul. 18 – 25

$261 CAD per night
Guest favourite

Home in New Lebanon

4.99 out of 5 average rating, 347 reviews

The old sawmill from 1771

Jul. 24 – 31

$209 CAD per night
Guest favourite

Barn in Hillsdale

4.97 out of 5 average rating, 116 reviews

Hudson Valley Hilltop Barn

Apr. 17 – 24

$1,354 CAD per night
Superhost

Apartment in Great Barrington

4.95 out of 5 average rating, 131 reviews

GB Eclectic Victorian

Dec. 4 – 11

$313 CAD per night
Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Feb. 26 – Mar. 5

$119 CAD per night
Guest favourite

Guest suite in Great Barrington

5.0 out of 5 average rating, 42 reviews

Sweet 1-bedroom with salt water pool

May 11 – 18

$238 CAD per night
Guest favourite

Apartment in Great Barrington

5.0 out of 5 average rating, 10 reviews

King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires

May 4 – 11

$197 CAD per night
Guest favourite

Home in Great Barrington

4.93 out of 5 average rating, 67 reviews

Quiet home on the hill.

Nov. 10 – 17

$260 CAD per night
Guest favourite

Barn in Great Barrington

5.0 out of 5 average rating, 45 reviews

Serene Renovated Barn w/ Firepit

Sep. 5 – 12

$345 CAD per night
Guest favourite

Guesthouse in Great Barrington

4.97 out of 5 average rating, 90 reviews

Studio in Bucolic Berkshire Setting

May 24 – 31

$210 CAD per night

Quick stats about vacation 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