A lake surrounded by autumn-colored trees and hills.

Find Cheap Hotels in Cheshire, MA from CA $100

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Cheshire Cheap Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Cheshire cheap hotels

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

1. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (1,002 reviews)
"Outstanding bed and breakfast in Williamstown, walking distance to the college, and also close to Mass MOCA. Will be staying there again. The fresh fruit was absolutely outstanding."
United States
Anuj
The price is CA $118
CA $132 total
includes taxes & fees
Nov 1 - Nov 2
Willows Motel Williamstown
A motel with a two-story structure, a covered parking area, and a well-maintained lawn with flower beds.

2. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (964 reviews)
"Very clean and welcoming room. Staff man was very helpful and conscientious"
United States
Frank
The price is CA $105
CA $123 total
includes taxes & fees
Nov 3 - Nov 4
Cozy Corner Motel
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

3. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (939 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is CA $113
CA $127 total
includes taxes & fees
Nov 26 - Nov 27
Berkshire Inn
A garden with a swing set, a blue chair, and a flower bed.

4. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (645 reviews)
"Perfect charming little hotel The couple at the front was very nice and helpful"
United States
yeraldine
The price is CA $139
CA $155 total
includes taxes & fees
Nov 3 - Nov 4
Maple Terrace Motel
Two Adirondack chairs facing a river with a forested hill in the background.

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
"The location was good for our trip."
United States
Basil
The price is CA $133
CA $149 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

6. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is CA $169
CA $390 total
includes taxes & fees
Oct 28 - Oct 29
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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.
View all properties

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great"
Anna 1-night trip
Posted 6 hours ago
Vacation Village in the Berkshires

Frequently asked questions

What is Cheshire like for travelers on a budget?
Discover cheap places to stay in Cheshire on Expedia.com and plan a vacation that stays within your budget. You can browse a wide offering of hotels and other accommodations with Member Prices to find the best deal for you. With our site's handy page filters, you can search by your price range, or by amenities that customers often look for like free breakfast and free parking. If you're hoping for reasonable options around local sights, such as Mount Greylock State Reservation or Cheshire Reservoir, try out the location filters to narrow down your search. As you browse, click the heart button to keep track of your favorites so that you can come back to them when you're ready to book. Interested in a car or a flight too? Take a look at the vacation packages available under Bundle and Save and discover huge discounts by reserving transportation at the same time.
When is the best time for a budget trip to Cheshire?
Weather will likely play an important role when you plan your trip to Cheshire, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to see and do in Cheshire?
You won't have to spend a fortune to find places to visit in Cheshire. You can budget for the local attractions that interest you most, and then make time for sights and activities that are easy on the wallet. If you're eager to get outdoors, you can enjoy the natural setting at Mount Greylock State Reservation, Cheshire Reservoir, or Mount Greylock State Reservation Visitor Center.
How can I get to Cheshire and get around on a budget?
Scoping out the transportation options in Cheshire can help keep you on budget. The closest airport is Pittsfield, MA (PSF-Pittsfield Municipal), situated 11.5 mi (18.5 km) away. However, if that doesn't suit your budget, you can arrange flights in and out of Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. Cheshire may not have many public transit options so a rental car could be a reasonable alternative to explore more of the area.

Explore a world of travel with Expedia