Great Barrington Vacation Rentals

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Vacation Rentals in Great Barrington

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge MA

With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.

Kitchen

Washer

Cozy Riverside Berkshires Retreat

Great Barrington MA

$329 nightly

$368 total

Aug 10 - Aug 11

Total with taxes and fees

Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic River.

Kitchen

Washer

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

East Chatham NY

Located in East Chatham, this vacation home is in the mountains, within a 15-minute drive of Queechy Lake and The Mac-Haydn Theatre.

Hot Tub

Kitchen

Lakefront Summer Stunner in New England Just 2 Hours From NYC

Sharon CT

Located in Sharon, this vacation home is on the waterfront, a 1-minute drive from Indian Lake and 6 minutes from North East Town Hall.

Kitchen

Pet friendly

Peace and quiet on the lake

Becket MA

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.

Kitchen

Washer

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Winchester CT

With a stay at this vacation home in Winsted, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 9 minutes by foot from The Marina at Highland Lake.

Kitchen

Washer

Amazing Backyard Escape, 10 Minutes from Stockbridge | Cordelia by AvantStay

Lee MA

With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

Kitchen

Washer

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

Chatham NY

$361 nightly

$404 total

Aug 9 - Aug 10

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

Charming Farmhouse - quiet, private & peaceful

Worthington MA

Located in Worthington, this vacation home is a 4-minute drive from Hiram H. Fox Wildlife Management Area and 6 minutes from Fox Den Wildlife Management Area.

Kitchen

Washer

Hearts Desire is your private escape.

Lanesborough MA

With a stay at this vacation home in Lanesborough, you'll be on a lake, within a 10-minute drive of Jiminy Peak Mountain Resort and Cheshire Reservoir.

Hot Tub

Kitchen

NEW: Chic Modern Barn Style Home in Fun Area

Pine Plains NY

$724 nightly

$818 total

Aug 4 - Aug 5

Total with taxes and fees

Located in Pine Plains, this vacation home is in the mountains, within a 5-minute drive of The Stissing Center and Pine Plains Library.

Kitchen

Washer

Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake

Copake Lake NY

With a stay at this vacation home in Hillsdale, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.

Kitchen

Washer

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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.