Windsor Holidays
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Windsor Holiday
Our pick of the best Windsor Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$206 per night from 27 May to 28 May
NZ$206
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (947 reviews)
"Everything great"
Reviewed on 24 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$238 per night from 27 May to 28 May
NZ$238
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (959 reviews)
"Great location, clean and spacious room, lobby area was very relaxing! We enjoyed the coffee available at the front as well."
Reviewed on 24 May 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$183 per night from 28 May to 29 May
NZ$183
28 May - 29 May
includes taxes & fees
8.8/10 Excellent! (2,367 reviews)
"The room was great. Had a kitchen, huge jetted tub, and private bedroom. Great area! I don't like paying resort fees for things we don't use though. It was raining and we arrived late at night. The indoor pool was amazingly crowded for 10pm. Must have been at least 25 people, including younger children. ..."
Reviewed on 25 May 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.
