Cheshire Vacations
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Find the Best Cheshire Vacation Packages
Cheshire Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is ₩139,686 per night from Oct 20 to Oct 21
₩139,686
₩171,495 total
Oct 20 - Oct 21
includes taxes & fees
8.6/10 Excellent! (2,013 reviews)
"Always very relaxing. Kids love the pool and we enjoy the hot tub and views"
Reviewed on Sep 21, 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is ₩203,830 per night from Oct 26 to Oct 27
₩203,830
₩227,678 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
a gem
"Totally perfect for mass mocha"
Reviewed on Sep 21, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is ₩131,389 per night from Sep 28 to Sep 29
₩131,389
₩178,254 total
Sep 28 - Sep 29
includes taxes & fees
8.8/10 Excellent! (656 reviews)
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."
Reviewed on Sep 25, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
