Cheshire, MA

Travel Guide

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..
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..
Cheshire Lake during a sunny winter day.
An amazing view of Cheshire from the too of a small mountain. It was a strenuous hike and a dangerous trip back down in snow and ice, but well worth it!
I'm not exactly sure what this is, but they all have giant smoke stacks.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night from Jan 25 to Jan 26
$141 total
Jan 25 - Jan 26
Total with taxes and fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,208 reviews)
It is one of my favorite places to go but sometimes it is overcrowded and the people can be rude and rowdy. But the staff is fantastic they do a great job even with the crowds.

Reviewed on Jan 16, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$130 nightly
The price is $145 total per night from Feb 1 to Feb 2
$145 total
Feb 1 - Feb 2
Total with taxes and fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (812 reviews)
Wonderful night!! Staff go out of their way to help you!!

Reviewed on Jan 17, 2026

Berkshire Mountain Lodge
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
$186 nightly
The price is $208 total per night from Jan 25 to Jan 26
$208 total
Jan 25 - Jan 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (563 reviews)
Everything was excellent

Reviewed on Jan 16, 2026

The Williams Inn
See all 991 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
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,208 reviews)
It is one of my favorite places to go but sometimes it is overcrowded and the people can be rude and rowdy. But the staff is fantastic they do a great job even with the crowds.

Reviewed on Jan 16, 2026

Vacation Village in the Berkshires
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
10/10 Exceptional! (7 reviews)
Healthy food too!

Reviewed on Oct 20, 2025

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 WiFi, free parking, and a fitness center. Popular attractions The Mount and Wyndhurst Golf & Club are located ...
8.4/10 Very Good! (139 reviews)
Condo was a great space. Bathroom walls should be repainted as stains are evident. There were also stains on the couch which I cleaned.

Reviewed on Jan 3, 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

5/5(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.

St Mary's of the Assumption Church

Cities near Cheshire

A fun night at the Dalton Carnival!

Dalton

Deer Hill Shelter is a backpackers shelter, and therefore FREE, unlike the other camp areas on Mt Greylock. It's only about a mile and half from the parking area nearest to Campground Trail. Deer Hill Trail itself branches off from Campground Trail to take you to the shelter. Map location is approximate since it doesn't show all the trails and the shelter is dwarfed by the surrounding forest. First come, first serve here ... and if you show up in the middle of the week in early summer, you might get it all to yourself like we did!

New Ashford

Highest point in the State of Massachusetts Mt. Greylock is at elevation 3791’. It is also located along the Georgia to Maine Appalachian Trail.

Adams

Great trail for a bike ride

Lanesborough

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