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.
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 €108 per night from 8 Feb to 9 Feb
€108
8 Feb - 9 Feb
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 ...
8.6/10 Excellent! (2,222 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.

Reviewed on 25 Jan 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is €112 per night from 8 Feb to 9 Feb
€112
8 Feb - 9 Feb
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! (826 reviews)
Room was clean and nicely equipped with kitchen. Will return if the future.

Reviewed on 1 Feb 2026

Berkshire Mountain Lodge
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
The price is €208 per night from 1 Mar to 2 Mar
€208
1 Mar - 2 Mar
includes taxes & fees
Stay at this business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ...
9.6/10 Exceptional! (572 reviews)
Clean

Reviewed on 31 Jan 2026

The Williams Inn
See all 1,006 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 ...
8.6/10 Excellent! (2,222 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.

Reviewed on 25 Jan 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 ...
9.2/10 Wonderful! (8 reviews)
Healthy food too!

Reviewed on 20 Oct 2025

Huttopia Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd Hancock MA
Stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular attractions ...
8.2/10 Very Good! (989 reviews)
This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ...

Reviewed on 5 Oct 2025

Jiminy Peak Mountain Resort
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

Explore a world of travel with Expedia