Winchester 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 Winchester
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
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Located in Plymouth, this cottage is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.
Kitchen
Washer
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 |
|---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | 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, Guest Cottage on Country Estate |