Winchester Holidays
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Photo by Donny Campos
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)
Nice and quiet. Friendly desk staff. It was nice to have a restaurant on site, but breakfast should start earlier than 8.
Reviewed on 8 Dec 2025
The Covered Bridge Inn
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is 2.085.257 ₫ per night from 24 Dec to 25 Dec
2.085.257 ₫
2.293.782 ₫ total
24 Dec - 25 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 4.823.473 ₫ per night from 26 Dec to 27 Dec
4.823.473 ₫
5.387.819 ₫ total
26 Dec - 27 Dec
includes taxes & fees
8.6/10 Excellent! (878 reviews)
Lovely night.
Reviewed on 10 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.
