Cheshire Holidays

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Top hotels in Cheshire

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is S$248 per night from 30 Jun to 1 Jul
S$248
30 Jun - 1 Jul
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"No real breakfast"

Reviewed on 21 Jun, 2026

Hotel Downstreet, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is S$183 per night from 23 Jun to 24 Jun
S$183
23 Jun - 24 Jun
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 Jun, 2026

The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is S$183 per night from 6 Jul to 7 Jul
S$183
6 Jul - 7 Jul
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 Jun, 2026

Vacation Village in the Berkshires
See all 987 properties in Cheshire
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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