A lake surrounded by autumn-colored trees and hills.

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Check availability on Cheshire Cheap Hotels

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
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 two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.
A white two-story building with a porch, labeled as a motel.
A hay bale display with pumpkins and scarecrows.

1. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
Charlene
CA $120
CA $134 total
includes taxes & fees
Nov 1 - Nov 2
Willows Motel Williamstown
An outdoor seating area with Adirondack chairs and potted plants.
A sign with the word "CLARM" on a grassy field with a road and trees in the background.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

2. 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 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.

3. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Kristina
CA $114
CA $127 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Inn
A garden with a swing set, a blue chair, and a flower bed.
A swimming pool with lounge chairs and a fence.
A house with a porch, snow-covered ground, and a Christmas tree with lights.
A breakfast buffet setup with cereal, milk, juice, and pastries.

4. 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 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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
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 $136
CA $152 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
View all properties

Top Cheshire Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"It was fine. No breakfast that I saw"
Michael 1-night trip
Posted 12 hours ago
Best Western Plus Berkshire Hills Inn & Suites
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."
Marti 1-night trip
Posted 17 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Property was clean, staff was knowledgeable and cordial. Parking was very easy."
Julia 1-night trip
Posted 19 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"
Woodward 2-night trip
Posted 2 days ago
Quality Inn Lee - Lenox South

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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