Photo by Ed Gaffny

Search Motels in Cheshire

Compare 21 Motels in Cheshire with updated reviews, rates, and availability.

Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (704)
"Manager was helpful. The heating system was loud and although the manager tried to fix it , the noise disrupted sleep. "
The price is SAR 297
SAR 331 total
includes taxes & fees
1 Jan - 2 January 2025
Howard Johnson by Wyndham Lenox
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (687)
"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 SAR 259
SAR 289 total
includes taxes & fees
28 Dec - 29 Dec
FairBridge Inn Express
The Villager Motel
Front of property

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (675)
"Clean, comfortable & easy to find. "
The price is SAR 259
SAR 289 total
includes taxes & fees
29 Dec - 30 Dec
The Villager Motel
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (754)
"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 SAR 323
SAR 361 total
includes taxes & fees
5 Jan - 6 January 2025
Berkshire Inn
Willows Motel Williamstown
Room

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (889)
"The room was clean,the bed comfortable. Since it is an older motel it could use a little updates. But it was clean as well as the bathroom and shower. Had a decent continental breakfast. Coffee maker was available in the room. Owner was very nice and welcoming."
The price is SAR 297
SAR 331 total
includes taxes & fees
29 Dec - 30 Dec
Willows Motel Williamstown
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 SAR 225
SAR 252 total
includes taxes & fees
30 Dec - 31 Dec
Econo Lodge Lee - Great Barrington
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (540)
"Nice place we will be back,"
The price is SAR 353
SAR 394 total
includes taxes & fees
16 Jan - 17 January 2025
Maple Terrace Motel
Cozy Corner Motel
Room

Cozy Corner Motel

2.0 star property
9.0 out of 10, Wonderful, (775)
"Adorable motel - super cute & rooms are spotless - convenient to Williamstown too…"
The price is SAR 282
SAR 332 total
includes taxes & fees
2 Jan - 3 January 2025
Cozy Corner Motel
Williamstown Motel
Front of property

Williamstown Motel

2.0 star property
8.6 out of 10, Excellent, (589)
"Owner was very friendly. Room were roomy. Clean "
The price is SAR 397
SAR 443 total
includes taxes & fees
16 Jan - 17 January 2025
Williamstown 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 SAR 259
SAR 289 total
includes taxes & fees
28 Dec - 29 Dec
Wagon Wheel Inn
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 SAR 591
SAR 625 total
includes taxes & fees
1 Jan - 2 January 2025
Blue Vista Motor Lodge
Berkshire Travel Lodge
Exterior

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (387)
"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 SAR 247
SAR 266 total
includes taxes & fees
12 Jan - 13 January 2025
Berkshire Travel 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 SAR 221
SAR 243 total
includes taxes & fees
31 Dec - 1 January 2025
Pleasant Valley Motel West Stockbridge
Howard Johnson by Wyndham Williamstown
Exterior

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (827)
"U"
The price is SAR 375
SAR 419 total
includes taxes & fees
29 Dec - 30 Dec
Howard Johnson by Wyndham Williamstown
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 SAR 300
SAR 335 total
includes taxes & fees
31 Dec - 1 January 2025
Sunset Inn
Heart of the Berkshires
Front of property

Heart of the Berkshires

The price is SAR 237
SAR 317 total
includes taxes & fees
30 Dec - 31 Dec
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 SAR 345
SAR 512 total
includes taxes & fees
28 Dec - 29 Dec
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.
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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, (1750)
"Nice and quiet family get a way"
The price is SAR 704
SAR 810 total
includes taxes & fees
1 Jan - 2 January 2025
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 SAR 710
SAR 779 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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. FairBridge Inn Express: Central Cheshire is 6.7 mi (10.8 km) away. Free WiFi and free parking are available during your stay, along with room amenities like a microwave. Willows Motel Williamstown: 10.1 mi (16.2 km) from the heart of Cheshire. Enjoy access to the library, and freebies including breakfast, 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 The Bookstore. 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.