Windsor Holidays
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Top hotels in Windsor
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is €98 per night from 2 Nov to 3 Nov
€98
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (2,057 reviews)
"This place is just beyond incredible! It is our 40th wedding anniversary today and so happy we found this place."
Reviewed on 13 Oct 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is €125 per night from 12 Nov to 13 Nov
€125
12 Nov - 13 Nov
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
Reviewed on 9 Oct 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is €109 per night from 5 Nov to 6 Nov
€109
5 Nov - 6 Nov
includes taxes & fees
8.8/10 Excellent! (687 reviews)
"Nice place to stay"
Reviewed on 9 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.
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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.
