Windsor Holidays
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Windsor Holiday
Our pick of the best Windsor Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 29 Apr to 30 Apr
NZ$217
29 Apr - 30 Apr
includes taxes & fees
8.8/10 Excellent! (2,328 reviews)
great stay.
Reviewed on 9 Apr 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is NZ$259 per night from 13 Apr to 14 Apr
NZ$259
13 Apr - 14 Apr
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Nice staff comfy bed nice views
Reviewed on 8 Apr 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$203 per night from 10 May to 11 May
NZ$203
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (897 reviews)
Love that place. Does need a little sprucing up. Staff great and accomodating
Reviewed on 5 Apr 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.
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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.
