Cheshire

Travel Guide

A lake surrounded by autumn-colored trees and hills.
A lake with lily pads and reeds, surrounded by autumn-colored trees and hills.
A lake surrounded by autumn-colored trees with a clear sky.
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
Fully refundableReserve now, pay when you stay
The price is €99 per night from 13 Aug to 14 Aug
€99
13 Aug - 14 Aug
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 ...
8.8/10 Excellent! (2,507 reviews)
"Had no issues with the room or property. We enjoyed our stay very much. Only Thing, I would say is the pull out couch was not comfortable for my son (you can feel the springs), but we brought a blow up mattress for emergency use which came in handy. I also mentioned my silver Expedia status (per ..."

Reviewed on 5 Aug 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is €169 per night from 20 Aug to 21 Aug
€169
20 Aug - 21 Aug
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! (1,008 reviews)
"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. ..."

Reviewed on 5 Aug 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is €140 per night from 24 Aug to 25 Aug
€140
24 Aug - 25 Aug
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 ...
Berkshire Mountain Lodge
See all 997 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 aparthotel in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in ...
8.8/10 Excellent! (2,507 reviews)
"Had no issues with the room or property. We enjoyed our stay very much. Only Thing, I would say is the pull out couch was not comfortable for my son (you can feel the springs), but we brought a blow up mattress for emergency use which came in handy. I also mentioned my silver Expedia status (per ..."

Reviewed on 5 Aug 2026

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 ...
Berkshire Mountain Lodge
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! (14 reviews)
"Wonderful experience for our family and dog. Kids loved the pool and games as well as smores by our camp fire each night. It's a relaxed property that is perfect for a family stay and truly relaxing to be so remote and connected to nature. Our dog loved the trails too. We will be back!"

Reviewed on 3 Aug 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.

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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