Winchester Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 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! (1,000 reviews)
Friendly stadd
Reviewed on Dec 25, 2025
The Covered Bridge Inn
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is ₩134,349 per night from Jan 23 to Jan 24
₩134,349
₩147,785 total
Jan 23 - Jan 24
includes taxes & fees
7.6/10 Good! (1,000 reviews)
Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street.
Reviewed on Dec 21, 2025
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is ₩193,054 per night from Jan 3 to Jan 4
₩193,054
₩212,360 total
Jan 3 - Jan 4
includes taxes & fees
8.4/10 Very Good! (747 reviews)
Comfortable room
Reviewed on Dec 28, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
