Cheshire Travel Guide

Tourist 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.
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.
The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is ₹8,839 per night from 9 Mar to 10 Mar
₹8,839
₹10,878 total
9 Mar - 10 Mar
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! (2,283 reviews)
Looks way better in person than the pictures. Still old and dated but not as spooky as the pictures seem. They don't tell you this at all, just expect you to read a packet - there is no housekeeping, no nothing. You are supposed to take your own trash out. They also do not really clean the room beforehand ...

Reviewed on 7 Mar 2026

Vacation Village in the Berkshires
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 ₹10,840 per night from 31 Mar to 1 Apr
₹10,840
₹12,109 total
31 Mar - 1 Apr
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,005 reviews)
For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options.

Reviewed on 5 Mar 2026

Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is ₹9,756 per night from 1 Apr to 2 Apr
₹9,756
₹12,948 total
1 Apr - 2 Apr
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (869 reviews)
The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after ...

Reviewed on 6 Mar 2026

Berkshire Mountain Lodge
See all 999 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! (2,283 reviews)
Looks way better in person than the pictures. Still old and dated but not as spooky as the pictures seem. They don't tell you this at all, just expect you to read a packet - there is no housekeeping, no nothing. You are supposed to take your own trash out. They also do not really clean the room beforehand ...

Reviewed on 7 Mar 2026

Vacation Village in the Berkshires
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 ...
Huttopia Berkshires
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this condo in Lenox. Enjoy free Wi-Fi, free parking and a fitness centre. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (141 reviews)
I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ...

Reviewed on 9 Feb 2026

The Ponds at Foxhollow
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

Cities near Cheshire

Wahconah Falls in the Berkshires

Dalton

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