Winchester Vacations
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Better together
Save up to ₩234,741 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
The price is ₩202,928 per night from Oct 1 to Oct 2
₩202,928
₩226,682 total
Oct 1 - Oct 2
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
Fantastic rest stop.
"Very quiet and spacious with appealing surroundings."
Reviewed on Sep 24, 2025
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is ₩176,355 per night from Oct 5 to Oct 6
₩176,355
₩191,345 total
Oct 5 - Oct 6
includes taxes & fees
8.4/10 Very Good! (901 reviews)
"Wonderful stay very nice place comfortable bed."
Reviewed on Sep 18, 2025
Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
8.2/10 Very Good! (889 reviews)
"The hotel was clean and organized but I found the HVAC unit full of black mold. The bed made my back hurt."
Reviewed on Sep 20, 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.
