Sheffield Cottages

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Cottages in Sheffield

Two Bedroom Cottage Close To Town

Sharon CT

Located in Sharon, this cottage is a 4-minute drive from Bodhi Tree Gallery and 7 minutes from TriArts Sharon Playhouse.

Huson Valley Group Getaway w/ Mtn Views + Fire Pit

Hudson NY

With a stay at this cottage in Hudson, you'll be within a 15-minute drive of Claverack Library and Stoddard Corner.

Cozy, private and modern Cottage

Hudson NY

Located in Hudson, this cottage is a 1-minute drive from Claverack Library and 6 minutes from Stoddard Corner.

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

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Canaan NY

Located in Canaan, this cottage is on the waterfront, a 3-minute drive from Queechy Lake and 7 minutes from Furnace Brook Winery at Hilltop Orchards.

Kitchen

Pet friendly

Creekside Cottage The Fitz House Red Hook NY

Red Hook NY

Located in Red Hook, this cottage is on a river, within a 15-minute drive of Lake Carvel and Lake Taghkanic State Park.

Kitchen

Pet friendly

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.

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.

Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville CT

Located in Lakeville, this cottage is on a lake, a 4-minute drive from Holley-Williams House Museum and 6 minutes from North East Town Hall.

Step back in time with our 2-bedroom cottage in charming New Hartford!

New Hartford CT

Located in New Hartford, this cottage is a 4-minute drive from Brodie Park and 7 minutes from Ames Plaza Shopping Center.

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.