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

Cozy, private and 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

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

Cozy Cottage-Sunset On The Lake

Otis MA

When you stay at this cottage in Otis, you'll be on a lake, within a 5-minute drive of County Beach and Otis Ridge.

Kitchen

Washer

Waterfront Cottage at Highland Lake w/dock

Winsted CT

A stay at this cottage places you in the heart of Winchester, steps from Highland Lake and 9 minutes by foot from The Marina at Highland Lake.

Kitchen

Free WiFi

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

2-bedroom cottage close to skiing with gas fireplace

New Marlborough MA

With a stay at this cottage in New Marlborough, you'll be within a 5-minute walk of New Marlborough Town Library and New Marlborough Town Hall.

Kitchen

Washer

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

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

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

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Becket MA

Located in Becket, this cottage is a 4-minute drive from Iroquis Waterfront and 8 minutes from Becket Quarry.

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.