Winchester Vacations
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Better together
Save up to ￥45,448 when you book a flight and hotel together*
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Find the Best Winchester Vacation Packages
Winchester Hotel Deals
The Colonial Hotel
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,009 reviews)
"Very convenient location. Facility is clean and attractive. Very comfortable."
Reviewed on Sep 16, 2025
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is ￥17,177 per night from Sep 29 to Sep 30
￥17,177
￥18,637 total
Sep 29 - Sep 30
includes taxes & fees
8.4/10 Very Good! (900 reviews)
"Wonderful stay very nice place comfortable bed."
Reviewed on Sep 18, 2025
Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
The price is ￥20,007 per night from Sep 29 to Sep 30
￥20,007
￥22,008 total
Sep 29 - Sep 30
includes taxes & fees
8/10 Very Good! (886 reviews)
"Clean room and great breakfast"
Reviewed on Sep 19, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
