Photo by Ed Gaffny

Search Motels in Cheshire

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare Motels in Cheshire with updated reviews, rates, and availability.

FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (695)
"Clean room quick easy check in"
The price is AED 253
AED 283 total
includes taxes & fees
10 Jan - 11 Jan
FairBridge Inn Express
The Villager Motel
Front of property

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (678)
"Very comfortable room in a lovely town! Easy check in and check out."
The price is AED 253
AED 283 total
includes taxes & fees
12 Jan - 13 Jan
The Villager Motel
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (705)
"The room was clean and spacious. The parking lot still had a lot of snow and especially ice"
The price is AED 290
AED 324 total
includes taxes & fees
10 Jan - 11 Jan
Howard Johnson by Wyndham Lenox
Willows Motel Williamstown
Room

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (894)
"Nice cozy place"
The price is AED 305
AED 341 total
includes taxes & fees
12 Jan - 13 Jan
Willows Motel Williamstown
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (758)
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."
The price is AED 316
AED 353 total
includes taxes & fees
13 Jan - 14 Jan
Berkshire Inn
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (581)
"Was convenient and inexpensive. The back stairs were a little rickety. Also had to ring the bell to check in later in the evening, but was fine. Room was just the basics, but served the purpose for my one night stay. "
The price is AED 220
AED 246 total
includes taxes & fees
10 Jan - 11 Jan
Econo Lodge Lee - Great Barrington
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (541)
"Property is clean and well maintained. Family that owns it are all very kind. We came here for a short winter getaway and plan on returning in the summer as it has a pool and is close to a lot of hiking!"
The price is AED 345
AED 386 total
includes taxes & fees
12 Jan - 13 Jan
Maple Terrace Motel
Wagon Wheel Inn
Exterior

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (597)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
10 Jan - 11 Jan
Wagon Wheel Inn
Berkshire Travel Lodge
Exterior

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (388)
"Not the Ritz Carlton, but the manager was courteous and the room was clean and in decent shape. I'd stay there again."
The price is AED 241
AED 261 total
includes taxes & fees
22 Jan - 23 Jan
Berkshire Travel Lodge
Cozy Corner Motel
Room

Cozy Corner Motel

2.0 star property
9.0 out of 10, Wonderful, (776)
"This was a very good place to stay for a night. Solid facilities and kind staff. Would definitely recommend! "
The price is AED 272
AED 321 total
includes taxes & fees
2 Feb - 3 Feb
Cozy Corner Motel
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (958)
"The room and bathroom were very clean. "
The price is AED 217
AED 238 total
includes taxes & fees
14 Jan - 15 Jan
Pleasant Valley Motel West Stockbridge
Blue Vista Motor Lodge
Front of property

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (161)
"Our stay was excellent! The hole stay was excellent… we will definitely spread our recommendations with friends and family! Look forward to our next stay there!"
The price is AED 578
AED 611 total
includes taxes & fees
12 Jan - 13 Jan
Blue Vista Motor Lodge
Williamstown Motel
Front of property

Williamstown Motel

2.0 star property
8.6 out of 10, Excellent, (590)
"Owner was very friendly. Room were roomy. Clean "
The price is AED 348
AED 389 total
includes taxes & fees
3 Feb - 4 Feb
Williamstown Motel
Howard Johnson by Wyndham Williamstown
Exterior

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (828)
"U"
The price is AED 367
AED 410 total
includes taxes & fees
11 Jan - 12 Jan
Howard Johnson by Wyndham Williamstown
Sunset Inn
Outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (378)
"Quick and easy check in! The manager was friendly and helpful. "
The price is AED 264
AED 295 total
includes taxes & fees
14 Jan - 15 Jan
Sunset Inn
Heart of the Berkshires
Front of property

Heart of the Berkshires

8.0 out of 10, Very Good, (1)
"Very cute décor, not the most comfortable or fresh, but clean and easy self check in/out system (door has a code which is communicated in advance). Lots of food options short drive away."
The price is AED 255
AED 337 total
includes taxes & fees
14 Jan - 15 Jan
Heart of the Berkshires
Northside Motel
Balcony

Northside Motel

2.0 star property
6.6 out of 10, (109)
"Stayed here for Solid Sound Festival since it’s a 10 min drive to Mass MOCA. It was exactly what you’d expect from a motel. Clean and comfortable. Perfectly met our needs. Coffee, orange juice, water cooler, and some pastries were offered in the office in the morning. It also looked like they were in the process of upgrading as mattresses and other items were being removed from some of the room the morning we left. We’d stay here again."
Northside Motel
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"I liked how there was walking trails and shopping near by. "
The price is AED 356
AED 521 total
includes taxes & fees
10 Jan - 11 Jan
Becket Motel
The Springs Motel
Exterior

The Springs Motel

2.0 star property
8.8 out of 10, Excellent, (40)
"The outdoor fire pits and setting areas looked like a blast but it rained so we didn’t get a chance to hang outside. Next time! "
The Springs Motel
Green Valley Motel
Room

Green Valley Motel

2.0 star property
6.6 out of 10, (101)
"I felt that It was a dirty on the outisde and the paint chips on the outside took away the pleasant view of it "
Green Valley Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Cheshire
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Cheshire

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1752)
"So enjoyed this property and all the staff was always there to help in anyway!"
The price is AED 689
AED 792 total
includes taxes & fees
14 Jan - 15 Jan
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is AED 694
AED 762 total
includes taxes & fees
12 Jan - 13 Jan
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AED 551
AED 841 total
includes taxes & fees
10 Jan - 11 Jan
Berkshire Village Carriage House - Super Private!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What can I expect from a motel trip to Cheshire?
If you can’t find a motel in Cheshire, let Expedia help you find a motel or something similar from over 919 accommodations in the larger area. Simply use our search tools to filter by price per night or cost-saving amenities such as free parking and free breakfast.
What are motels like?
When you stay at a motel, you’ll often find an outdoor pool and a free parking spot. With a stay at a motel, you’ll usually access your room directly from the parking lot. The word “motel” was invented in 1925 by the owner of the Milestone Mo-Tel in San Luis Obispo, California.
What are the best motels in Cheshire?
These are some of Expedia customers’ favorite motels in the larger area. The Villager Motel is located 12.3 mi (19.9 km) from the heart of Cheshire. Enjoy the in-room free WiFi, and freebies including breakfast and parking. Howard Johnson by Wyndham Lenox: Free WiFi, free parking, and a 24-hour front desk are available during your stay. Central Cheshire is 12.2 mi (19.6 km) away. Berkshire Inn: Enjoy access to the seasonal outdoor pool, and freebies including WiFi and parking. Located 9.6 mi (15.5 km) from the heart of Cheshire. Willows Motel Williamstown: Central Cheshire is 10.1 mi (16.2 km) away. A library along with freebies like breakfast, WiFi, and parking are available during your stay. FairBridge Inn Express: 6.7 mi (10.8 km) from the heart of Cheshire. Enjoy access to the business center, and freebies including WiFi and parking.
What can I do in Cheshire?
Some outdoorsy places nearby include Mount Greylock State Reservation, Mount Greylock State Reservation Visitor Center, and Mount Greylock. You’ll find these family-friendly sights in the area: Berkshire Museum, Bousquet Ski Area, and Berkshire Scenic Railway Museum. While you’re checking out the area, consider visiting St Mary’s of the Assumption Church, Brodie Mountain, and Jiminy Peak Mountain Resort.
What's the weather like in Cheshire?
Weather can make or break a roadtrip, so here’s some data about year-round temperatures in Cheshire to help you plan yours: 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 are my options for getting around Cheshire when staying in a motel?
We’ve gathered some information about getting around Cheshire to help you navigate your stay: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) away from the city center. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you’d like to explore around the area, you may want a rental car for your journey.