Great Barrington Cottages

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Cottages in Great Barrington

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough MA

Located in Great Barrington, this cottage is on a lake, within a 5-minute drive of Lake Buel and Les Trois Emme Winery.

Kitchen

Washer

The Blue Elm - A Historic Berkshire Cottage

Sheffield MA

Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.

Kitchen

Free WiFi

Idillic summer getaway in Litchfield Hills, CT.

Sharon CT

When you stay at this cottage in Sharon, you'll be on a river, within a 5-minute drive of Housatonic Meadows State Park and West Cornwall Covered Bridge.

Kitchen

Washer

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Valatie NY

Located in Valatie, this cottage is on a lake, a 1-minute drive from Kinderhook Lake and 7 minutes from Valatie Free Library.

Kitchen

Pet friendly

Private hot tub + Modern Cottage

Hudson NY

Located in Hudson, this cottage is a 1-minute drive from Claverack Library and 6 minutes from Stoddard Corner.

Hot Tub

Kitchen

Waterfront Cottage 10 Min From Great Barrington

New Marlborough MA

With a stay at this cottage in Great Barrington, you'll be steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.

Kitchen

Washer

The Cottage at Highland Lake, year-round, waterfront with a boat dock

Winsted CT

With a stay at this cottage in Winchester, 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

Free WiFi

Ashley Falls Home w/ Fire Pit: Hike & Ski!

Ashley Falls MA

Located in Ashley Falls, this cottage is within a 5-minute drive of Ashley Falls Woods and Bartholomew's Cobble.

Kitchen

Parking included

Creekside Cottage The Fitz House Red Hook NY

Red Hook NY

Located in Red Hook, this cottage is on a river, within a 15-minute drive of Lake Carvel and Lake Taghkanic State Park.

Kitchen

Pet friendly

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA

With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from Larkum Pond.

Kitchen

Pet friendly

Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville CT

Located in Lakeville, this cottage is on a lake, a 4-minute drive from Holley-Williams House Museum and 6 minutes from North East Town Hall.

Kitchen

Washer

Riverfront Hudson Valley Gem w/ Beach Access!

Athens NY

Located in Athens, this cottage is a 1-minute drive from Hudson River and 9 minutes from Coxsackie Village Hall.

Kitchen

Pet friendly

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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.