Berkshire County Cottages

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Cottages in Berkshire County

Cozy Cottage-Sunset On The Lake

Otis MA

$515 nightly

$575 total

Oct 23 - Oct 24

Total with taxes and fees

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

Kitchen

Washer

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

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

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

Monterey MA

Located in Monterey, this cottage is a 1-minute drive from Lake Garfield and 7 minutes from Bidwell House Museum.

Washer

Dryer

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

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

Pine & Paddle | Pond Access • Kayaks

Pittsfield MA

With a stay at this cottage in Richmond, you'll be on a lake, within a 15-minute drive of Tanglewood Music Center and Tracy Brook Wildlife Sanctuary.

Kitchen

Washer

Peaceful Cabin Close to Skiing and Hiking

Otis MA

With a stay at this cottage in Otis, you'll be within a 10-minute drive of Jacob's Pillow and Handle Tow.

Kitchen

Dryer

2-bedroom cottage close to hiking and swimming with AC

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

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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.