Windsor Packages (Flight + Hotel)
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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 ฿3,013 per night from 2 Nov to 3 Nov
฿3,013
฿3,725 total
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (2,079 reviews)
"Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back."
Reviewed on 19 Oct 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is ฿3,061 per night from 2 Nov to 3 Nov
฿3,061
฿4,153 total
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (716 reviews)
"Yes, everything was very well set up. Thanks."
Reviewed on 19 Oct 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
The price is ฿3,383 per night from 2 Nov to 3 Nov
฿3,383
฿3,779 total
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (908 reviews)
"Enjoyed dinner and drinks"
Reviewed on 18 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.
