Winchester Cottages
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Cottages in Winchester
Peaceful Goshen Cottage w/ Screened Porch & Views!
With a stay at this cottage in Goshen, you'll be within a 5-minute drive of Goshen Historic District and Mohawk State Forest.
Kitchen
Washer
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.
Kitchen
Pet friendly
Newly renovated cottage on the lake!
With a stay at this cottage in Harwinton (Northwest Harwinton), you'll be a 3-minute drive from Harwinton Conservation and Recreation Area and 8 minutes from Warner Theater.
Kitchen
Washer
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.
Kitchen
Pet friendly
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.
Washer
Dryer
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.
Kitchen
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.
Kitchen
Free WiFi
Cozy 2-bedroom Cottage with Access to Bantam Lake
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 Camp Columbia State Park.
Kitchen
Washer
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.
Kitchen
Washer
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.
Kitchen
Pet friendly
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.
Winchester Cottages essential information
Accommodation | 68 Cottages |
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Lowest Price | |
Highest Price | |
Popular accommodation | Peaceful Goshen Cottage w/ Screened Porch & Views!, Private Island - Largest Fresh Water Reservoir in Mass...., Newly renovated cottage on the lake!, Idillic summer getaway in Litchfield Hills, CT., Quiet rustic cottage with shared lake access, East Otis Vacation Rental w/ Private Deck & BBQ!, The Cottage at Highland Lake, year-round, waterfront with a boat dock , Cozy 2-bedroom Cottage with Access to Bantam Lake, Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, West Cornwall Cabin ~ 4 Mi to Covered Bridge!, Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape, Perfect Vacation Get Away - Historical New Marlborough |