Winchester Holidays
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- Plan, book, travel with confidence
- Better togetherSave up to Rp173.195 when you book a flight and hotel together*
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Top hotels in Winchester
The Colonial Hotel
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,014 reviews)
Overall, everything was great. The room was large and clean. Had a chance to enjoy the pool and jacuzzi. Looking forward to going back again.
Reviewed on 2 Nov 2025
The Covered Bridge Inn
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is Rp1.533.152 per night from 9 Nov to 10 Nov
Rp1.533.152
Rp1.686.467 total
9 Nov - 10 Nov
includes taxes & fees
7.6/10 Good! (1,000 reviews)
Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests.
Reviewed on 3 Nov 2025
Travelodge by Wyndham Brattleboro VT
1254 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is Rp1.187.441 per night from 9 Nov to 10 Nov
Rp1.187.441
Rp1.306.186 total
9 Nov - 10 Nov
includes taxes & fees
5.8/10 (729 reviews)
Reasonable rate for the the accomadations.
Reviewed on 21 Oct 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
