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

Don't see what you're looking for?
See all available properties in Winchester
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.

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