A lake surrounded by autumn-colored trees and hills.

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Check availability on Cheshire Cheap Hotels

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 $358
CA $378 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 TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.
A dining area with wooden tables and chairs, a television, and a door with a sign.
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
Horace
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 bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
A cozy living room with a stone fireplace, comfortable seating, and a television.
A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

3. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $163
CA $179 total
includes taxes & fees
Sep 28 - Sep 29
The Springs Motel
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 two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with large windows, a fireplace, and a variety of seating options.

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Jacob
CA $134
CA $165 total
includes taxes & fees
Sep 28 - Sep 29
Vacation Village in the Berkshires
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, 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.
A hotel room with a desk, chair, TV, and a painting on the wall.
A single-story building with a porch, a chimney, and a satellite dish.

5. Rodeway Inn

Rodeway Inn
Adams
United States
Brandie
CA $108
CA $120 total
includes taxes & fees
Oct 11 - Oct 12
Rodeway Inn
A living room with a fireplace, two sofas, and four black side tables.
A dining area with a wooden table, four chairs, and a framed picture on the wall.
A two-story building with a symmetrical facade, large columns, and a central entrance.
A bedroom with a bed, a sofa, a fireplace, and a chandelier.

6. The Revival House

The Revival House
Adams
United States
Katrina
CA $234
CA $261 total
includes taxes & fees
Sep 27 - Sep 28
The Revival House
A building with a covered parking area and a grassy front yard.
A dining area with wooden chairs and tables, a kitchen counter with appliances, and framed pictures on the wall.
A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.
A motel with multiple rooms, a parking area, and a large tree in the foreground.

7. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
Williamstown
United States
Donna
CA $141
CA $157 total
includes taxes & fees
Sep 28 - Sep 29
Howard Johnson by Wyndham Williamstown
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
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.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

8. The Yankee Inn

The Yankee Inn
Lenox
United States
William
CA $148
CA $166 total
includes taxes & fees
Sep 28 - Sep 29
The Yankee Inn
A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.
A living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.
A kitchen with a fireplace, dining area, and a large window with curtains.

9. Williamstown Motel

Williamstown Motel
Williamstown
United States
Ahmet
CA $143
CA $160 total
includes taxes & fees
Sep 27 - Sep 28
Williamstown 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 residential street with a paved road, a lamp post, and flowering trees.

10. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Kristina
CA $116
CA $130 total
includes taxes & fees
Oct 26 - Oct 27
Berkshire Inn
View all properties

Top Cheshire Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"Toilet was faulty but they gave us another room. Not much variety on the breakfast"
Ron 3-night trip
Posted 16 hours ago
Hampton Inn & Suites Berkshires-Lenox
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"great for families"
Emily 1-night trip
Posted 19 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"No Pool or hot tub available"
Betty 1-night trip
Posted 20 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 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Great location for our trip into NE."
Mark 1-night trip
Posted 3 days ago
Quality Inn Lee - Lenox South
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 6 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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