Windsor Holidays
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Top hotels in Windsor
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 3.057.610 ₫ per night from 31 May to 1 Jun
3.057.610 ₫
4.003.696 ₫ total
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (956 reviews)
"The room was clean and comfortable, the staff was friendly and helpful..only negative is that the furniture in the room is in serious need of replacement… veneers on end tables lifting, upholstered kitchen chairs all had rips…"
Reviewed on 27 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 2.825.285 ₫ per night from 11 Jun to 12 Jun
2.825.285 ₫
3.155.843 ₫ total
11 Jun - 12 Jun
includes taxes & fees
9/10 Wonderful! (962 reviews)
"The converted motel has several appealing features — it was clean, the Le Labo products smelled wonderful, and the lobby bar is beautifully designed. Unfortunately, the level of service fell well below expectations. Two days before our arrival, I received a survey asking whether we’d like any additional ..."
Reviewed on 27 May 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is 3.132.193 ₫ per night from 11 Jun to 12 Jun
3.132.193 ₫
3.787.566 ₫ total
11 Jun - 12 Jun
includes taxes & fees
8.8/10 Excellent! (2,375 reviews)
"Clean room great check in process smooth easy going. Jacuzzi was great, very cleaned!"
Reviewed on 27 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.
