Winchester Holidays
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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! (1,000 reviews)
Room was clean, bed was nice
Reviewed on 16 Feb, 2026
Colonial Motel And Spa
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is S$125 per night from 5 Mar to 6 Mar
S$125
5 Mar - 6 Mar
includes taxes & fees
6.8/10 (1,003 reviews)
The room was old and run down. The building we were in was very sketchy. People next to us were up partying/noisy until all hours of the night, and there was a dog barking until 2:00am right below us. I had a horrible nights sleep. The pillows were flat as pancakes, the towels were the roughest/scratchiest ...
Reviewed on 24 Feb, 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is S$158 per night from 4 Mar to 5 Mar
S$158
4 Mar - 5 Mar
includes taxes & fees
8.2/10 Very Good! (948 reviews)
Staff and clean room
Reviewed on 22 Feb, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
