Berkshire County Cottages

Name: Spacious Historic Home in the Berkshires!
Address: Pittsfield

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Cottages in Berkshire County

Private Island - Largest Fresh Water Reservoir in Mass....

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.

East Otis Vacation Rental w/ Private Deck & BBQ!

With a stay at this cottage in Otis, you'll be steps from Otis Reservoir and a 3-minute drive from Larkum Pond.

Charming historic cottage on scenic road to Mt. Greylock

Located in Lanesborough, this cottage is in the mountains, a 3-minute drive from Mount Greylock State Reservation and 5 minutes from Mount Greylock State Reservation Visitor Center.

Cozy Berkshire cottage with fireplace.

Located in Pittsfield, this cottage is in the mountains, within a 5-minute drive of Guido's Marketplace and Berkshire Museum.

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

Located in Becket, this cottage is a 4-minute drive from Iroquis Waterfront and 6 minutes from October Mountain State Forest.

Perfect Vacation Get Away - Historical New Marlborough

Located in Great Barrington, this cottage is in a rural location, a 4-minute drive from Dry Hill and 5 minutes from New Marlborough Town Hall.

The Blue Elm - A Historic Berkshire Cottage

$416

includes taxes & fees

$372 per night

Jan 8 - Jan 9

Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.

Quiet rustic cottage with shared lake access

With a stay at this cottage in Great Barrington, you'll be on a lake, just steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

With a stay at this cottage in Monterey, you'll be within a 10-minute drive of Beartown State Forest and Bidwell House Museum.

Beachwood Cottage

Located in West Stockbridge, this cottage is on a lake, a 5-minute drive from Frelinghuysen Morris House and Studio and 6 minutes from Tanglewood Music Center.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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

Spacious Historic Home in the Berkshires!

With a stay at this cottage in Pittsfield, you'll be within a 10-minute walk of Colonial Theater and Berkshire Athenaeum.

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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.