Berkshire County Cottages

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Cottages in Berkshire County

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

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

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

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

A-frame Cabin w/ Furnished Deck in Becket!

Becket MA

Located in Becket, this cottage is a 3-minute drive from Pyramid Lake and 5 minutes from Jacob's Pillow.

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

Berkshire Hills Nature Lovers' Log Home Retreat

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

Berkshires Cabin 2 Mi to Appalachian Trail!

Otis MA

Located in Otis, this cottage is within a 15-minute drive of Jacob's Pillow and Pyramid Lake.

Kitchen

Parking included

Spacious Historic Home in the Berkshires!

Pittsfield MA

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

Kitchen

Washer

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Great Barrington 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

Pet friendly

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

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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.