Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Donny Campos

Top hotels in Winchester

The Colonial Hotel

The Colonial Hotel

3 out of 5
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 Colonial Hotel
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
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

Hampton Inn & Suites Greenfield
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
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

The Covered Bridge Inn
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.