A lake surrounded by autumn-colored trees and hills.

Find Cheap Hotels in Cheshire, MA from CA $98

  • 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

Our top choices for Cheshire cheap hotels

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $331
CA $350 total
includes taxes & fees
Jul 13 - Jul 14
Harbour House Inn
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is CA $94
CA $103 total
includes taxes & fees
Jul 22 - Jul 23
Pleasant Valley Motel West Stockbridge
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,004 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is CA $192
CA $214 total
includes taxes & fees
Jul 12 - Jul 13
Best Western Plus Berkshire Hills Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (848 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is CA $88
CA $98 total
includes taxes & fees
Jul 19 - Jul 20
FairBridge Inn Express
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (141 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is CA $161
CA $249 total
includes taxes & fees
Jul 14 - Jul 15
Blooming Inn
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (35 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is CA $235
CA $262 total
includes taxes & fees
Aug 9 - Aug 10
The Revival House
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."
United States
Brian
The price is CA $214
CA $239 total
includes taxes & fees
Jul 12 - Jul 13
The Yankee Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,009 reviews)
"Great place"
United States
Michelle
The price is CA $203
CA $226 total
includes taxes & fees
Jul 23 - Jul 24
Quality Inn Lee - Lenox South
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (486 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is CA $96
CA $107 total
includes taxes & fees
Jul 16 - Jul 17
Berkshire Travel Lodge
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
"Great place"
United States
Luciane
The price is CA $140
CA $157 total
includes taxes & fees
Jul 16 - Jul 17
Howard Johnson by Wyndham Lenox
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
"We absolutely love it there! Colleen at the front desk has been there a very long time she's sweet as can be! everyone is so nice and helpful, and the place is relaxing and clean we stay there quite often!"
nicole 3-night trip
Posted 3 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