Winchester Holidays
Book a Hotel + Flight or Car together to unlock savings
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
Hampton Inn & Suites Greenfield
184 Shelburne Rd Greenfield MA
Fully refundableReserve now, pay when you stay
The price is 4.829.518 ₫ per night from 17 Dec to 18 Dec
4.829.518 ₫
5.394.572 ₫ total
17 Dec - 18 Dec
includes taxes & fees
8.6/10 Excellent! (876 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
The Covered Bridge Inn
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is 2.087.870 ₫ per night from 13 Dec to 14 Dec
2.087.870 ₫
2.296.657 ₫ total
13 Dec - 14 Dec
includes taxes & fees
7.6/10 Good! (1,000 reviews)
Room very nice, comfortable clean
Reviewed on 29 Nov 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.
