Winchester Vacations
Book a Hotel + Flight or Car together to unlock savings
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- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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! (1,003 reviews)
Property was great
Reviewed on Nov 8, 2025
The Covered Bridge Inn
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is ￥13,041 per night from Nov 10 to Nov 11
￥13,041
￥14,345 total
Nov 10 - Nov 11
includes taxes & fees
7.6/10 Good! (1,002 reviews)
Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests.
Reviewed on Nov 3, 2025
Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is ￥13,992 per night from Dec 7 to Dec 8
￥13,992
￥15,391 total
Dec 7 - Dec 8
includes taxes & fees
8.2/10 Very Good! (916 reviews)
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Reviewed on Nov 4, 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.
