The Berkshires Cottages

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Cottages in The Berkshires

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.

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.

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

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

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro MA

With a stay at this cottage in Lanesborough, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.

Kitchen

Free WiFi

Massachusetts Vacation Rental w/ Deck & Grill

Windsor MA

With a stay at this cottage in Windsor, you'll be 8.1 mi (13 km) from Susan B. Anthony Birthplace Museum and 8.2 mi (13.2 km) from Tannery Falls.

Kitchen

Washer

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

325 Long Pond Road Great Barrington MA

Located in Great Barrington, this cottage is within a 10-minute drive of Art et Industrie and Housatonic River.

Kitchen

Washer

Light-filled cottage

New Marlborough MA

Located in New Marlborough, this cottage is on a lake, within a 15-minute drive of Cookson State Forest and Dry Hill.

Hot Tub

Kitchen

Luxury Vacation Rental in the Berkshires!

Williamstown MA

Located in Williamstown, this cottage is within a 5-minute drive of Mount Greylock State Reservation and Lower Linear Park.

Kitchen

Washer

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

21 Saint James Avenue Lee MA

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

Kitchen

Washer

Cozy Berkshire cottage with fireplace.

Pittsfield MA

With a stay at this cottage in Pittsfield, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Colonial Theater.

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.