Find Cheap Hotels in Cheshire, MA from CA $166

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Check availability on Cheshire Cheap Hotels

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7

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, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $315
CA $333 total
includes taxes & fees
May 27 - May 28
Harbour House Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $195
CA $214 total
includes taxes & fees
Jun 4 - Jun 5
Shaker Mill Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (958 reviews)
"Great stay!"
United States
Aditya
The price is CA $148
CA $166 total
includes taxes & fees
Jun 7 - Jun 8
Berkshires Untold
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, (1,003 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is CA $152
CA $170 total
includes taxes & fees
May 28 - May 29
Best Western Plus Berkshire Hills Inn & Suites
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is CA $215
CA $240 total
includes taxes & fees
May 25 - May 26
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, (1,006 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is CA $192
CA $215 total
includes taxes & fees
Jun 7 - Jun 8
The Yankee Inn
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (136 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 $133
CA $216 total
includes taxes & fees
May 27 - May 28
Blooming Inn
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (211 reviews)
"Great stay! "
United States
ALEKSey
The price is CA $247
CA $261 total
includes taxes & fees
May 27 - May 28
Blue Vista Motor Lodge
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
"Really clean, great staff. Pool & hot tub A+"
United States
Daniel
The price is CA $121
CA $166 total
includes taxes & fees
May 26 - May 27
Berkshire Mountain Lodge
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,006 reviews)
"Clean rooms and lovely view"
Canada
Laraib
The price is CA $171
CA $191 total
includes taxes & fees
May 28 - May 29
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Hotel staff extremely nice from the front desk to housekeeping. Hotel was very clean and looked fairly new. Our room was very large perfect for the 5 adults staying there."
Wendy 2-night trip
Posted less than an hour ago
Best Western Plus Berkshire Hills Inn & Suites

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 interested in affordable options near specific attractions, such as Mount Greylock State Reservation, try filtering by location to refine 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, Mount Greylock, or Wahconah Falls State Park.
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.

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