Great Barrington Vacation Rentals

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Vacation Rentals in Great Barrington

Cozy Riverside Berkshires Retreat

Great Barrington MA

$284 nightly

$317 total

Jun 17 - Jun 18

Total with taxes and fees

When you stay at this vacation home in Great Barrington, you'll be on a river, within a 15-minute drive of Norman Rockwell Museum and National Shrine of the Divine Mercy.

Kitchen

Washer

Lakefront Summer Stunner in New England Just 2 Hours From NYC

Sharon CT

Located in Sharon, this vacation home is on the waterfront, within a 10-minute drive of North East Town Hall and Veterans Field.

Kitchen

Pet friendly

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham NY

$333 nightly

$373 total

Jul 13 - Jul 14

Total with taxes and fees

Located in Chatham, this vacation home is a 5-minute drive from The Mac-Haydn Theatre and 8 minutes from Hudson Chatham Winery.

Washer

Dryer

Mountain View Getaway

West Cornwall CT

Located in Cornwall, this vacation home is on a lake, within a 15-minute drive of Music Mountain and West Cornwall Covered Bridge.

Kitchen

Washer

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

East Chatham NY

Located in East Chatham, this vacation home is within a 15-minute drive of Queechy Lake and New Lebanon Library.

Pool

Kitchen

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Austerlitz NY

Located in Hillsdale, this vacation home is in the mountains, within a 15-minute drive of Hillsdale Town Hall and Ebenezer II Gifts and Antiques.

Kitchen

Washer

The Meadows House @ Otis Ridge w/ 7-person hot tub

Otis MA

Located in Otis, this vacation home is in the mountains, a 2-minute drive from Otis Ridge and 5 minutes from Old Baldy Wildlife Sanctuary.

Hot Tub

Kitchen

Charming cottage with lake access, wood burning fire place, and WiFi

Elizaville NY

When you stay at this vacation home in Elizaville, you'll be 9 minutes by car from Tousey Winery.

Kitchen

Washer

Large Barn styled vacation home that fits groups with space to spare.

Craryville NY

With a stay at this vacation home in Copake Lake, you'll be on the waterfront, just a 1-minute walk from Copake Lake and 13 minutes by foot from Mosquito Island.

Kitchen

Washer

BRAND NEW 4 story home minutes from Warren St w/ a King Suite!

Hudson NY

With a stay at this vacation home in Hudson, you'll be within a 10-minute drive of Olana State Historic Site and Hudson Area Library.

Kitchen

Washer

Whispering Estate Guest House - Countryside Getaway

Goshen CT

$778 nightly

$882 total

Jun 14 - Jun 15

Total with taxes and fees

Located in Goshen, this vacation home is within a 10-minute drive of Mohawk State Forest and Goshen Historic District.

Kitchen

Washer

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington MA

With a stay at this vacation home, you'll be centrally located in Great Barrington, within a 15-minute drive of Norman Rockwell Museum and Monument Mountain.

Hot Tub

Kitchen

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.