Winchester Holidays
Photo by Donny Campos
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Top hotels in Winchester
The Colonial Hotel
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,003 reviews)
Easy checkin, pleasant staff and clean room.
Reviewed on 14 Dec 2025
The Covered Bridge Inn
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is €84 per night from 18 Dec to 19 Dec
€84
18 Dec - 19 Dec
includes taxes & fees
7.6/10 Good! (1,001 reviews)
Room very nice, comfortable clean
Reviewed on 29 Nov 2025
Hampton Inn & Suites Greenfield
184 Shelburne Rd Greenfield MA
Fully refundableReserve now, pay when you stay
The price is €174 per night from 22 Dec to 23 Dec
€174
22 Dec - 23 Dec
includes taxes & fees
8.6/10 Excellent! (877 reviews)
The Hampton Inn let us check-in two hours early after a winter snowstorm closed all the places we were to visit that day. We then hunkered down and watched the snow pile up from our room.
Reviewed on 3 Dec 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.
