A lake surrounded by autumn-colored trees and hills.

Find Cheap Hotels in Cheshire, MA from CA $99

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Check availability on Cheshire Cheap Hotels

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

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 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 hay bale display with pumpkins and scarecrows.

1. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
Charlene
CA $120
CA $135 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 swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A motel with a parking lot, a swimming pool, and outdoor seating.
A residential street with a paved road, a lamp post, and flowering trees.

2. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Kristina
CA $116
CA $130 total
includes taxes & fees
Nov 4 - Nov 5
Berkshire Inn
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 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.

3. Cozy Corner Motel

Cozy Corner Motel
Williamstown
United States
Jonathan
CA $106
CA $126 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 $141
CA $158 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 cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

5. The Yankee Inn

The Yankee Inn
Lenox
United States
William
CA $140
CA $156 total
includes taxes & fees
Oct 19 - Oct 20
The Yankee Inn
View all properties

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"I was pleasantly surprised by how nice it was there. The photos do not do it justice. It is a large resort with lots to do. Beautiful location, our room was amazing. Just a relaxing place to unwind and enjoy the beauty of the area."
Patricia 2-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"24-7 coffee was great"
wayne 2-night trip
Posted 5 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Room was clean, bed was comfortable, breakfast was good, centrally located for our days events!"
Chuck 1-night trip
Posted 1 day 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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