Sheffield Cottages

Name: The Cottage at Highland Lake, year-round, waterfront with a boat dock
Address: Winsted

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Cottages in Sheffield

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.

Idillic summer getaway in Litchfield Hills, CT.

When you stay at this cottage in Sharon, you'll be on a river, within a 5-minute drive of Housatonic Meadows State Park and West Cornwall Covered Bridge.

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.

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

Located in Cornwall, this cottage is within a 5-minute drive of Mohawk Mountain State Forest and Mohawk Mountain State Park.

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 1 - Jan 2, 2025

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

Cottage is currently rented for the year, and not available until further notice

Located in Norfolk, this cottage is a 1-minute drive from Great Mountain Forest and 6 minutes from Norfolk Historical Museum.

Pet friendly

Free WiFi

Country Cottage Retreat, Fido stays for free

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.

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.

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.

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.

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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.