Winsted Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cottages in Winsted

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

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

Bethlehem CT

With a stay at this cottage in Bethlehem, you'll be on a lake, just steps from Long Meadow Pond and a 3-minute drive from Bellamy-Ferriday House and Garden.

Kitchen

Free WiFi

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.

Kitchen

Washer

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Plymouth CT

Located in Plymouth, this cottage is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.

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

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

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

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

Charming, private 2-bedroom cottage on classic New England farm in Washington CT

Washington CT

Located in Washington Depot, this cottage is in a rural location, within a 10-minute drive of Institute for American Indian Studies Museum and Research Center and Church Hill.

Kitchen

Washer

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

Guest Cottage on Country Estate

Watertown CT

With a stay at this cottage, you'll be centrally located in Watertown, within a 10-minute drive of Lake Winnemaug and Black Rock State Park.

Kitchen

Washer

Cozy 2-bedroom Cottage with Access to Bantam Lake

Morris CT

With a stay at this cottage in Morris, you'll be on a lake, just steps from Bantam Lake and a 2-minute drive from Bantam Cinema & Arts Center.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Winsted

View all properties

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.