Cheshire

Travel Guide

An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.
Cheshire
Cheshire
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
The price is €167 per night from 30 Jun to 1 Jul
€167
30 Jun - 1 Jul
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
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
The price is €124 per night from 23 Jun to 24 Jun
€124
23 Jun - 24 Jun
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! (1,004 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
The price is €123 per night from 6 Jul to 7 Jul
€123
6 Jul - 7 Jul
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
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 980 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.
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 condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
8.8/10 Excellent! (2,405 reviews)
"Traveled with my 3 kids and husband for a family weekend getaway. The staff was friendly and welcoming. My kids had a great time at the playground and the indoor pool. We didn't use the outdoor pool as it was still a bit cold outside. The room was spacious and clean. Overall, had a wonderful experience ..."

Reviewed on 21 Jun 2026

Vacation Village in the Berkshires
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT
Stay at this apartment in Whitingham. Enjoy free breakfast, a sauna and laundry facilities. Popular attractions Harriman Reservoir and Readsboro Community Library ...
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."

Reviewed on 25 May 2026

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
Stay at this campsite in Williamstown. Enjoy free parking, breakfast (surcharge) and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
9.4/10 Exceptional! (10 reviews)
"Excelente servicio"

Reviewed on 8 Mar 2026

Huttopia Berkshires
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.

Popular places to visit

St Mary's of the Assumption Church

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.

St Mary's of the Assumption Church

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