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! (1,019 reviews)
"Huge place. Great restaurant and quiet area"
Reviewed on 1 Oct 2025
Econo Lodge Brattleboro
515 Canal St, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is 1.793.304 ₫ per night from 2 Nov to 3 Nov
1.793.304 ₫
1.972.634 ₫ total
2 Nov - 3 Nov
includes taxes & fees
5.4/10 (568 reviews)
Fine room, right next to I-91 exit.
"Nothing bad about inside the room (108) -- but it was next to the hallway to the stairs to the second floor, so heard occasional foot-stomps during the evening. No other noises, though. Spatious double sinks, very unusual. Huge, firm bed. The manager has quite the beautiful flowers and vegetables ..."
Reviewed on 2 Sept 2025
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is 2.824.870 ₫ per night from 2 Nov to 3 Nov
2.824.870 ₫
3.064.984 ₫ total
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (908 reviews)
"Very clean, up to date, affordable"
Reviewed on 29 Sept 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.
