Cheshire

Travel Guide

A lake surrounded by autumn-colored trees and hills.
A lake surrounded by autumn-colored trees with a clear sky.
A lake with lily pads and reeds, surrounded by autumn-colored trees and hills.
A rural road with a double yellow line, surrounded by green fields and trees, under a partly cloudy sky.
A frozen lake with a group of ducks swimming in the center.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is HK$630 per night from 15 Nov to 16 Nov
HK$630
HK$790 total
15 Nov - 16 Nov
includes taxes & fees
Stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in ...
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is HK$602 per night from 6 Dec to 7 Dec
HK$602
HK$848 total
6 Dec - 7 Dec
includes taxes & fees
Stay at this golf aparthotel in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,269 reviews)
"Everything was great!"

Reviewed on 12 Nov 2026

Berkshire Mountain Lodge
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 HK$988 per night from 12 Dec to 13 Dec
HK$988
HK$1,104 total
12 Dec - 13 Dec
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,001 reviews)
"Breakfast was h asic everything else was perfect"

Reviewed on 12 Nov 2026

The Yankee Inn
See all 986 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.
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire MA
Stay at this holiday home in Cheshire. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Cheshire Reservoir ...
9.6/10 Exceptional! (101 reviews)
"This is a special spot for our family. We've stayed here twice and look forward to our next visit!"

Reviewed on 13 Sept 2026

19th c. Barn in the Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in ...
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Stay at this golf aparthotel in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,269 reviews)
"Everything was great!"

Reviewed on 12 Nov 2026

Berkshire Mountain Lodge
See all 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.

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

10.0/10 (1 review)
St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views or seek out its ski slopes.
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