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 20 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, (678)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is AED 290
AED 324 total
includes taxes & fees
28 Nov - 29 Nov
FairBridge Inn Express
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (747)
"Nice area "
The price is AED 316
AED 353 total
includes taxes & fees
1 Dec - 2 Dec
Berkshire Inn
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (701)
"It served our needs"
The price is AED 290
AED 324 total
includes taxes & fees
1 Dec - 2 Dec
Howard Johnson by Wyndham Lenox
Willows Motel Williamstown
Room

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (882)
"Convient to Williams College"
The price is AED 305
AED 341 total
includes taxes & fees
28 Nov - 29 Nov
Willows Motel Williamstown
Cozy Corner Motel
Room

Cozy Corner Motel

2.0 star property
9.0 out of 10, Wonderful, (771)
"The hotel room was acceptable but not really anything special. Beautiful grounds around the building. Not much within walking distance. The host couldn't have been kinder and more interested in making our stay pleasant."
The price is AED 262
AED 309 total
includes taxes & fees
2 Dec - 3 Dec
Cozy Corner 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
28 Nov - 29 Nov
Wagon Wheel Inn
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (578)
"We were looking for a place not too expensive to just spend the night. This place fit the bill; clean and comfy. Bathroom needed some work and the floors were quite slippery, just coming in from the bad weather. Nothing a few scatter rugs and bathmat could fix. Bed was comfortable and a nice little dining table for 2 near the window. We'd stay there again."
The price is AED 220
AED 246 total
includes taxes & fees
1 Dec - 2 Dec
Econo Lodge Lee - Great Barrington
Howard Johnson by Wyndham Williamstown
Exterior

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (824)
"Very nice, very convenient."
The price is AED 367
AED 410 total
includes taxes & fees
28 Nov - 29 Nov
Howard Johnson by Wyndham Williamstown
The Villager Motel
Front of property

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (670)
"Clean, comfortable & easy to find. "
The price is AED 253
AED 283 total
includes taxes & fees
1 Dec - 2 Dec
The Villager Motel
Williamstown Motel
Front of property

Williamstown Motel

2.0 star property
8.6 out of 10, Excellent, (585)
"The room was clean and the owner was very friendly and accommodating. The location was convenient for our short trip. The rate was reasonable. "
The price is AED 290
AED 324 total
includes taxes & fees
28 Nov - 29 Nov
Williamstown Motel
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (536)
"Very kind owners. Friendly atmosphere. "
The price is AED 349
AED 390 total
includes taxes & fees
1 Dec - 2 Dec
Maple Terrace Motel
Berkshire Travel Lodge
Exterior

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (384)
"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 248
AED 268 total
includes taxes & fees
11 Dec - 12 Dec
Berkshire Travel Lodge
Blue Vista Motor Lodge
Front of property

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (157)
"We loved it! Wish we stayed longer. Beautiful views, very quiet and relaxing. Helpful and friendly staff. Everything we needed for a nice getaway. Only disappointment was that we checked out the morning before the aurora borealis. That would have made it over the top!"
The price is AED 578
AED 611 total
includes taxes & fees
1 Dec - 2 Dec
Blue Vista Motor Lodge
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (956)
"Well located near attractions "
The price is AED 217
AED 238 total
includes taxes & fees
2 Dec - 3 Dec
Pleasant Valley Motel West Stockbridge
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
1 Dec - 2 Dec
Becket Motel
Sunset Inn
Outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (376)
"When we arrived, the receptionist was pleasant and kind, our room was ready. When we asked for more towels, we did not have to wait for more than 5 minutes and we had them. The restaurant next door, Rose's cafe, is amazing!"
The price is AED 264
AED 295 total
includes taxes & fees
1 Dec - 2 Dec
Sunset Inn
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
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
The Weathervane Motel
Property grounds

The Weathervane Motel

2.0 star property
7.2 out of 10, Good, (128)
"Booked a king bed but when I got there they told me no cable in that room. They gave me a room with a double bed that were on top of being small were very uncomfortable plus so much dust in air conditioner my allergies were affected plus it stunk couldn’t stay had to repack and go drive around and find a clean hotel plus staff never used a mask or gloves when I went back next day because I forgot my meds in drawer He told me he already cleaned room and there was nothing in the room I walked past...
The Weathervane 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, (1746)
"Property was beautiful, great staff "
The price is AED 620
AED 717 total
includes taxes & fees
1 Dec - 2 Dec
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, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 657
AED 721 total
includes taxes & fees
28 Nov - 29 Nov
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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 889 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. Berkshire Inn is located 9.6 mi (15.5 km) from the heart of Cheshire. Enjoy access to the seasonal outdoor pool, and freebies including WiFi and parking. FairBridge Inn Express: Free WiFi and free parking are available during your stay, along with room amenities like a microwave. Central Cheshire is 6.7 mi (10.8 km) away. Howard Johnson by Wyndham Lenox: Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Located 12.2 mi (19.6 km) from the heart of Cheshire. Howard Johnson by Wyndham Williamstown: Central Cheshire is 9.7 mi (15.6 km) away. A business center along with freebies like breakfast, WiFi, and parking are available during your stay. The Villager Motel: 12.3 mi (19.9 km) from the heart of Cheshire. Enjoy the in-room free WiFi, and freebies including breakfast 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.