Stockbridge Cottages

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Cottages in Stockbridge

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.

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.

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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.

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Outdoor Space

Charming historic cottage on scenic road to Mt. Greylock

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.

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.

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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

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.

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Welcome to the Red Bridge Cottage!

Located in Valatie, this cottage is in a rural location, within a 10-minute drive of Shaker Museum and Library and Valatie Free Library.

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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

Dec 2 - Dec 3

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

Fun Getaway Lakehouse in the Hudson Valley

Located in Copake Lake, this cottage is on a lake, a 1-minute drive from Copake Lake and 7 minutes from Mosquito Island.

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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.

Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!

Located in Copake Lake, this cottage is on a lake, a 1-minute drive from Copake Lake and 7 minutes from Mosquito Island.

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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.