Sheffield Cottages

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Cottages in Sheffield

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

Located in Otis, this cottage is on the waterfront, a 1-minute drive from Otis Reservoir and 5 minutes from County Beach.

Pet friendly

Fireplace

East Otis Vacation Rental w/ Private Deck & BBQ!

Located in Otis, this cottage is a 1-minute drive from Otis Reservoir and 8 minutes from County Beach.

Outdoor Space

Kitchen

Cozy cottage with kettle pond lake 2 minutes away

When you stay at this cottage in Norfolk, you'll be within a 10-minute drive of Norfolk Historical Museum and Infinity Music Hall and Bistro.

Pet friendly

Free WiFi

Two Bedroom Cottage Close To Town

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

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.

Pet friendly

Outdoor Space

Cottage in the Berkshires 10 min. to Great Barrington

Located in Great Barrington, this cottage is on the waterfront, within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Pet friendly

Free WiFi

Perfect Vacation Get Away - Historical New Marlborough

$150

per night

Jun 6 - Jun 7

Located in Great Barrington, this cottage is in a rural location, a 4-minute drive from Dry Hill and 7 minutes from Questing.

Pet friendly

Fireplace

The Blue Elm - A Historic Berkshire Cottage

$250

per night

Jun 6 - Jun 7

With a stay at this cottage in Sheffield, you'll be within a 5-minute drive of Housatonic River and Ashley House.

Fireplace

Free WiFi

Country Cottage Retreat

Located in Red Hook, this cottage is in a rural location, within a 10-minute drive of Red Hook Golf Club and Center for Performing Arts at Rhinebeck.

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.

Fireplace

Outdoor Space

The Cottage at Highland Lake, year-round, waterfront with a boat dock

With a stay at this cottage in Winsted, you'll be on the waterfront, just steps from Highland Lake and a 2-minute drive from Winchester Historical Society.

Free WiFi

Outdoor Space

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.

Fireplace

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.