
Winchester Holidays
Photo by Donny Campos
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Save up to S$134 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
8.6/10 Excellent! (1,005 reviews)
"This Hotel is like an Old Family Friend. It’s our go to when we are staying in the area. Friendly staff. Comfortable rooms."
Reviewed on 5 Jul, 2025

Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is S$137 per night from 10 Jul to 11 Jul
S$137
10 Jul - 11 Jul
includes taxes & fees
6.6/10 (1,002 reviews)
"We like the room. Nice and spacious. Er"
Reviewed on 2 Jul, 2025

Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is S$178 per night from 20 Jul to 21 Jul
S$178
20 Jul - 21 Jul
includes taxes & fees
8/10 Very Good! (841 reviews)
"Great for the price"
Reviewed on 28 Jun, 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.
Frequently asked questions
* 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.