Sheffield Cottages

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Cottages in Sheffield

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.

Kitchen

Washer

Cozy, private and modern Cottage

Hudson NY

Located in Hudson, this cottage is a 1-minute drive from Claverack Library and 7 minutes from Columbia-Greene Hospital Foundation.

Hot Tub

Kitchen

Two Bedroom Cottage Close To Town

Sharon CT

$398 nightly

$451 total

Oct 21 - Oct 22

Total with taxes and fees

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

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

Mtn-view Retreat in Huson Valley: Great for Groups

Hudson NY

With a stay at this cottage in Hudson, you'll be within a 15-minute drive of Claverack Library and Columbia-Greene Hospital Foundation.

Kitchen

Washer

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

Cozy Cottage-Sunset On The Lake

Otis MA

$514 nightly

$574 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

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

Craryville NY

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

Washer

Dryer

Bluestone Cottage | Historic Goshen Retreat with Saltwater Pool, Cozy Charm & Year Round Adventures

Goshen CT

Located in Goshen, this cottage is within a 5-minute drive of Goshen Historic District and Woodridge Lake.

Pool

Kitchen

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 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

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

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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.