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
The price is S$201 per night from 29 Jun to 30 Jun
S$201
29 Jun - 30 Jun
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Although the property is older, it is kept very clean. All the bedding and mattresses seemed brand new and were very comfortable. The front desk staff and restaurant staff were very nice and the food was great! It has that small New England town feel and is very welcoming."
Reviewed on 25 Jun, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is S$191 per night from 29 Jun to 30 Jun
S$191
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (908 reviews)
"Perfect location. The hotel itself is historic but feels dated because of gaps in maintenance. Lack of restaurant is noted though lots of options just outside the property. Staff at the front desk is very friendly and provided great recommendations."
Reviewed on 24 Jun, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
The price is S$168 per night from 28 Jun to 29 Jun
S$168
28 Jun - 29 Jun
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"Everything was great except that the room's bathroom floor was still wet, presumably from the previous occupant."
Reviewed on 25 Jun, 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.
Stay near popular Winchester attractions
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