Photo by Ed Gaffny

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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 24 Motels in Cheshire with updated reviews, rates, and availability.

Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (716)
"No issues"
The price is AED 253
AED 283 total
includes taxes & fees
24 Mar - 25 Mar
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (839)
"Such nice people who run it. Nothing fancy but the people who work there are so friendly and accommodating "
The price is AED 331
AED 369 total
includes taxes & fees
24 Mar - 25 Mar
Howard Johnson by Wyndham Williamstown
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (690)
"The front desk staff was really nice and check in was very quick. My king bed room was great. It smelled fresh and was very clean. There’s a mini fridge, coffee maker, and a microwave. The bathroom was stocked nicely with towels and soaps as well as a hair dryer. Outside there are cute chairs and some swings on the property. This was a very budget friendly place and will definitely come back again!"
The price is AED 253
AED 283 total
includes taxes & fees
24 Mar - 25 Mar
The Villager Motel
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (764)
"The room was very clean "
The price is AED 316
AED 353 total
includes taxes & fees
24 Mar - 25 Mar
Berkshire Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (710)
"Friendly staff and quick checkin "
The price is AED 253
AED 283 total
includes taxes & fees
24 Mar - 25 Mar
FairBridge Inn Express
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (548)
"This is a great place to escape to in the Berkshires. Convenient location, quiet neighborhood, and great spots to eat."
The price is AED 345
AED 386 total
includes taxes & fees
24 Mar - 25 Mar
Maple Terrace Motel
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.0 out of 10, Wonderful, (801)
"Love this place. Have stayed at least ten times and K just keeps improving the rooms and facility in general."
The price is AED 309
AED 363 total
includes taxes & fees
25 Mar - 26 Mar
Cozy Corner Motel
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (906)
"Great motel, very clean, and great staff. recommended!"
The price is AED 294
AED 329 total
includes taxes & fees
6 Apr - 7 Apr
Willows Motel Williamstown
Blue Vista Motor Lodge
Single Room | In-room safe, desk, free WiFi, bed sheets

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (166)
"We had such a great stay at the Blue Vista Motor Lodge. The staff we encountered were welcoming and lovely. The room was super clean and had everything we needed for a comfortable stay. And the view! Incredible. "
The price is AED 578
AED 611 total
includes taxes & fees
24 Mar - 25 Mar
Blue Vista Motor Lodge
Pleasant Valley Motel West Stockbridge
Garden view

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (964)
"The room and bathroom were very clean. "
The price is AED 223
AED 245 total
includes taxes & fees
27 Mar - 28 Mar
Pleasant Valley Motel West Stockbridge
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (398)
"Staff friendly and helpful. "
The price is AED 241
AED 261 total
includes taxes & fees
5 Apr - 6 Apr
Berkshire Travel Lodge
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (600)
"Great location. Pleasant staff."
The price is AED 217
AED 242 total
includes taxes & fees
30 Mar - 31 Mar
Wagon Wheel Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (587)
"While the gentleman at the front desk can be a bit cold, the women that work at the property are very pleasant. They were super accommodating and did a nice job cleaning the room during our stay. The room was a good value and provided a nice place for our family of 5 plus a small dog to lay our heads at night."
The price is AED 239
AED 267 total
includes taxes & fees
24 Mar - 25 Mar
Econo Lodge Lee - Great Barrington
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (380)
"The room was clean and perfect for our stay."
The price is AED 301
AED 336 total
includes taxes & fees
24 Mar - 25 Mar
Sunset Inn
Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (253)
"Very nice Mom & Pop motel in a convenient location. "
The price is AED 290
AED 324 total
includes taxes & fees
24 Mar - 25 Mar
Williamstown Motel
Heart of the Berkshires
Economy Cabin | Premium bedding, individually decorated, free WiFi, bed sheets

Heart of the Berkshires

9.4 out of 10, Exceptional, (3)
"Was great comfy quiet "
The price is AED 310
AED 402 total
includes taxes & fees
24 Mar - 25 Mar
Heart of the Berkshires
The Springs Motel
Courtyard

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 price is AED 418
AED 459 total
includes taxes & fees
24 Mar - 25 Mar
The Springs 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 349
AED 513 total
includes taxes & fees
24 Mar - 25 Mar
Becket Motel
Northside Motel
Exterior

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
Green Valley Motel
Free WiFi, bed sheets, alarm clocks

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

19th c. Barn in the Berkshires
Interior

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (85)
"Amazing property, very clean- "
19th c. Barn in the Berkshires
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Very nice accomodations, more like a mini apartment than a motel room. "
The price is AED 474
AED 560 total
includes taxes & fees
25 Mar - 26 Mar
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, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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 954 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. Howard Johnson by Wyndham Williamstown is located 9.7 mi (15.6 km) from the heart of Cheshire. Enjoy access to the business center, and freebies including breakfast, WiFi, and parking. The Villager Motel: Free breakfast, free WiFi, and free parking are available during your stay. Central Cheshire is 12.3 mi (19.9 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. Maple Terrace Motel: Central Cheshire is 10.2 mi (16.4 km) away. A seasonal outdoor pool along with freebies like breakfast, WiFi, and parking are available during your stay. Berkshire Inn: 9.6 mi (15.5 km) from the heart of Cheshire. Enjoy access to the seasonal outdoor pool, 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 Hopkins Observatory. While you’re checking out the area, consider visiting St Mary’s of the Assumption Church, Wahconah Falls State Park, and Brodie Mountain.
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.