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 S$147 per night from 2 Nov to 3 Nov
S$147
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (2,046 reviews)
"Nice room clean and friendly staff"
Reviewed on 10 Oct, 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is S$192 per night from 10 Nov to 11 Nov
S$192
10 Nov - 11 Nov
includes taxes & fees
8.6/10 Excellent! (999 reviews)
a gem
"Totally perfect for mass mocha"
Reviewed on 21 Sept, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is S$164 per night from 2 Nov to 3 Nov
S$164
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (693 reviews)
"The room is nice and clean, good parking, quiet environment"
Reviewed on 12 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. 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.
