A lake surrounded by autumn-colored trees and hills.

Find Cheap Hotels in Cheshire, MA from CA $87

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Check availability on Cheshire Cheap Hotels

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Cheshire cheap hotels

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.
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.
A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.

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 garden with a swing set, a blue chair, and a flower bed.
A garden with a wooden pergola, potted plants, and a lawn with chairs.
A swimming pool with lounge chairs and a fence.
A house with a porch, snow-covered ground, and a Christmas tree with lights.

2. Maple Terrace Motel

Maple Terrace Motel
Williamstown
United States
Deborah
CA $141
CA $157 total
includes taxes & fees
Nov 1 - Nov 2
Maple Terrace Motel
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A residential street with a paved road, a lamp post, and flowering trees.

3. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Linda
CA $120
CA $134 total
includes taxes & fees
Nov 14 - Nov 15
Berkshire Inn
An outdoor seating area with Adirondack chairs and potted plants.
A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

4. 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 modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

5. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
CA $142
CA $159 total
includes taxes & fees
Oct 28 - Oct 29
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 $164
CA $392 total
includes taxes & fees
Oct 15 - Oct 16
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
View all properties

Top Cheshire Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Clean room. Special thank you to the cleaning and breakfast staff. Great balcony view. We will come back again."
Christopher 2-night trip
Posted 3 hours ago
The Yankee Inn
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Had a comfortable stay."
Lucinda 2-night trip
Posted 4 hours ago
Quality Inn Lee - Lenox South
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"
Viviane 2-night trip
Posted 21 hours ago
Vacation Village in the Berkshires
FairBridge Inn Express

FairBridge Inn Express

8/10 Good
"Room was clean . Overall property was average but expected for the price"
Edward 2-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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