Berkshire County Cottages

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Cottages in Berkshire County

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

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

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.

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.

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

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.

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.

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.

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.

Beachwood Cottage

Stockbridge MA

With a stay at this cottage in West Stockbridge, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and Stockbridge Bowl.

Lakefront Otis Home w/ Stunning Views & Boats!

Otis MA

When you stay at this cottage in Otis, you'll be within a 10-minute drive of Ashintully Gardens and McLennan Reservation.

1 Mi to Dtwn: Beautiful Home in Williamstown!

Williamstown MA

With a stay at this cottage in Williamstown, you'll be a 5-minute walk from Colonial Plaza and 14 minutes by foot from Lower Linear Park.

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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.