A lake surrounded by autumn-colored trees and hills.

Find Cheap Hotels in Cheshire, MA from CA $100

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Check availability on Cheshire Cheap Hotels

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Cheshire cheap hotels

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.
A white two-story building with a porch, labeled as a motel.
A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.
A hay bale display with pumpkins and scarecrows.

1. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
David
CA $120
CA $134 total
includes taxes & fees
Nov 1 - Nov 2
Willows Motel Williamstown
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.
A motel with a parking lot, a swimming pool, and outdoor seating.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

2. Berkshire Inn

Berkshire Inn
Pittsfield
United States
cheryl
CA $117
CA $130 total
includes taxes & fees
Nov 18 - Nov 19
Berkshire Inn
An outdoor seating area with Adirondack chairs and potted plants.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A sign with the word "CLARM" on a grassy field with a road and trees in the background.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

3. Cozy Corner Motel

Cozy Corner Motel
Williamstown
United States
Jonathan
CA $106
CA $125 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Corner Motel
A garden with a swing set, a blue chair, and a flower bed.
A swimming pool with lounge chairs and a fence.
A garden with a wooden pergola, potted plants, and a lawn with chairs.
A breakfast buffet setup with cereal, milk, juice, and pastries.

4. Maple Terrace Motel

Maple Terrace Motel
Williamstown
United States
Deborah
CA $140
CA $156 total
includes taxes & fees
Nov 1 - Nov 2
Maple Terrace Motel
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

5. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
CA $133
CA $148 total
includes taxes & fees
Oct 19 - Oct 20
The Yankee Inn
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.
A red building with a green door labeled "Apartment 1," a small garden with mulch and plants, and a white car parked in the background.
A modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.
A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.

6. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
CA $179
CA $408 total
includes taxes & fees
Oct 19 - Oct 20
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
View all properties

Top Cheshire Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"
Julio 1-night trip
Posted 2 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Would stay here again for sure"
Jennifer 1-night trip
Posted 16 hours ago
Hotel Downstreet, an Ascend Collection Hotel
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
Richard 1-night trip
Posted 3 days ago
FairBridge Inn Express

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.

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