A lake surrounded by autumn-colored trees and hills.

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Check availability on Cheshire Cheap Hotels

Tonight
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Cheshire cheap hotels

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.
A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.
A gazebo in a lush garden with flowering plants and a large tree.
A gazebo in a garden with a house in the background.

1. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
CA $359
CA $379 total
includes taxes & fees
Sep 28 - Sep 29
Harbour House Inn
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A hotel room with a desk, computer, TV, and a chair.
A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

2. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
William
CA $88
CA $98 total
includes taxes & fees
Sep 28 - Sep 29
FairBridge Inn Express
A patio area with outdoor furniture, a fire pit, and potted plants.
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A cozy living room with a stone fireplace, comfortable seating, and a television.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

3. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $158
CA $173 total
includes taxes & fees
Sep 28 - Sep 29
The Springs Motel
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.
A reception desk with a computer, a monitor, and a sign about Choice Privileges.
A hotel room with a desk, chair, TV, and a painting on the wall.
A room with a door, a table with a chair, a window with blinds, and an air conditioning unit.

4. Rodeway Inn

Rodeway Inn
Adams
United States
Brandie
CA $108
CA $121 total
includes taxes & fees
Oct 4 - Oct 5
Rodeway Inn
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A spacious living room with large windows, a fireplace, and a variety of seating options.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

5. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Jacob
CA $135
CA $166 total
includes taxes & fees
Sep 29 - Sep 30
Vacation Village in the Berkshires
A living room with a fireplace, two sofas, and four black side tables.
A doorway leading to a room with a fireplace, a sofa, and decorative wall sconces.
A bedroom with a bed, a sofa, a fireplace, and a chandelier.
A two-story building with a symmetrical facade, large columns, and a central entrance.

6. The Revival House

The Revival House
Adams
United States
Katrina
CA $234
CA $262 total
includes taxes & fees
Sep 28 - Sep 29
The Revival House
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

7. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
COLLEEN
CA $112
CA $125 total
includes taxes & fees
Sep 28 - Sep 29
Howard Johnson by Wyndham Lenox
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.
A residential street with a paved road, a lamp post, and flowering trees.
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.

8. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Kristina
CA $122
CA $136 total
includes taxes & fees
Sep 28 - Sep 29
Berkshire Inn
A wooden cabin with a covered deck, a fire pit, and string lights.
A swimming pool with a wooden deck, lounge chairs, and umbrellas.
A wooden cabin with a porch and a small deck, surrounded by trees in a forest.

9. Huttopia Berkshires

Huttopia Berkshires
Williamstown
United States
Dandara
CA $98
CA $110 total
includes taxes & fees
Sep 29 - Sep 30
Huttopia Berkshires
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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

10. The Yankee Inn

The Yankee Inn
Lenox
United States
William
CA $149
CA $166 total
includes taxes & fees
Sep 28 - Sep 29
The Yankee Inn
View all properties

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"No issues"
Steven 1-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Typical every day hotel, but clean and comfortable bed. Water pressure could be better."
Brian 1-night trip
Posted 2 hours ago
Quality Inn Lee - Lenox South
The Yankee Inn

The Yankee Inn

10/10 Excellent
"There was a nice set up for the complimentary breakfast."
Allison 2-night trip
Posted 4 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 4 days ago
Hotel Downstreet, an Ascend Collection Hotel
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 8 days ago
Howard Johnson by Wyndham Lenox

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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