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.
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.
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 €121 per night from 5 Apr to 6 Apr
€121
5 Apr - 6 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! (1,003 reviews)
Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ...

Reviewed on 22 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 €107 per night from 24 Mar to 25 Mar
€107
24 Mar - 25 Mar
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! (884 reviews)
This is our 3rd year staying here for my son’s birthday in March. Affordable and having the 2 rooms with a kitchen is so nice. My son’s favorite part is the pool which is always warm and clean, never smells too strong like some places. Hot tub feels amazing too. Will be back next year, or sooner ...

Reviewed on 22 Mar 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is €67 per night from 1 Apr to 2 Apr
€67
1 Apr - 2 Apr
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (880 reviews)
Wonderful place, great toiletries and great friendly staff. We will be back

Reviewed on 22 Mar 2026

Berkshires Untold
See all 1,017 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.
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
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
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 ...
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