Windsor Vacations
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Find the Best Windsor Vacation Packages
Windsor Hotel Deals
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is ￥26,152 per night from Jun 14 to Jun 15
￥26,152
￥29,212 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Clean simple, functional, nice all day coffee tea station"
Reviewed on Jun 8, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ￥22,532 per night from Jul 12 to Jul 13
￥22,532
￥28,755 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (973 reviews)
"Staff, breakfast, spaciousness of the room, all fabulous."
Reviewed on Jun 11, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is ￥20,680 per night from Jun 14 to Jun 15
￥20,680
￥24,859 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (2,392 reviews)
"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent ..."
Reviewed on Jun 8, 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.
