Cheshire Holidays
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Cheshire Holiday
Our pick of the best Cheshire Hotel Deals
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is NZ$335 per night from 30 June to 1 July
NZ$335
30 June - 1 July
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"No real breakfast"
Reviewed on 21 June 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$248 per night from 23 June to 24 June
NZ$248
23 June - 24 June
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"The only tiny complaint is that there was no maple syrup for the waffles. Everything else was fantastic!"
Reviewed on 21 June 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$236 per night from 25 June to 26 June
NZ$236
25 June - 26 June
includes taxes & fees
8.8/10 Excellent! (2,406 reviews)
"Everything was top. Can't think of anything to improve. Hope we can return, certainly we'll try"
Reviewed on 22 June 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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- Charlemont Holidays
- Goose Pond Reservation
- Massachusetts Museum of Contemporary Art
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- G. William Pitt House and Collection
- Deerfield Academy
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- Historical Old NMH Campus Building #3
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- National Shrine of the Divine Mercy
- Greenfield Community College
- Sterling and Francine Clark Art Institute
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- Williams College
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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.
