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! (1,004 reviews)
Yes
Reviewed on 16 Nov 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 30 Nov to 1 Dec
4.829.518 ₫
5.394.571 ₫ total
30 Nov - 1 Dec
includes taxes & fees
8.6/10 Excellent! (873 reviews)
Check in was great!
Reviewed on 13 Nov 2025
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is 3.775.038 ₫ per night from 30 Nov to 1 Dec
3.775.038 ₫
4.152.543 ₫ total
30 Nov - 1 Dec
includes taxes & fees
8.2/10 Very Good! (920 reviews)
Yes
Reviewed on 16 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.
