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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

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, (717)
"Staff friendly. Room comfortable. Location great."
The price is AED 253
AED 283 total
includes taxes & fees
20 Apr - 21 Apr
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 367
AED 410 total
includes taxes & fees
19 Apr - 20 Apr
Howard Johnson by Wyndham Williamstown
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (696)
"We stayed 2 nights. The staff were great . The non smoking rooms were awesome, very clean. Plenry of Hot water too.. Best value for yhe money 💰 Highly recommend...✌️🤠 "
The price is AED 253
AED 283 total
includes taxes & fees
20 Apr - 21 Apr
The Villager Motel
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (712)
"Friendly staff and quick checkin "
The price is AED 261
AED 292 total
includes taxes & fees
1 May - 2 May
FairBridge Inn Express
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (765)
"The location is convenient for the Pittsfield area and the room was very comfortable. "
The price is AED 316
AED 353 total
includes taxes & fees
20 Apr - 21 Apr
Berkshire Inn
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.0 out of 10, Wonderful, (807)
"The staff was super friendly. The room was very clean. Overall, a great experience. "
The price is AED 290
AED 342 total
includes taxes & fees
18 May - 19 May
Cozy Corner Motel
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (551)
"We were in Williamstown for a college tour, two adults three children, we had two rooms in this hotel , and it was just what we needed. Rooms big enough and in a good state, and a nice outside area. "
The price is AED 364
AED 406 total
includes taxes & fees
21 Apr - 22 Apr
Maple Terrace Motel
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 234
AED 257 total
includes taxes & fees
22 Apr - 23 Apr
Pleasant Valley Motel West Stockbridge
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 228
AED 255 total
includes taxes & fees
24 Apr - 25 Apr
Econo Lodge Lee - Great Barrington
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 278
AED 310 total
includes taxes & fees
1 May - 2 May
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, (169)
"Lovely stay!"
The price is AED 656
AED 693 total
includes taxes & fees
20 Apr - 21 Apr
Blue Vista Motor Lodge
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (400)
"Staff friendly and helpful. "
The price is AED 248
AED 268 total
includes taxes & fees
1 May - 2 May
Berkshire Travel Lodge
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 331
AED 369 total
includes taxes & fees
29 Apr - 30 Apr
Sunset Inn
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (601)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
19 Apr - 20 Apr
Wagon Wheel Inn
Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (255)
"Welcoming staff, great location."
The price is AED 290
AED 324 total
includes taxes & fees
20 Apr - 21 Apr
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 "
Heart of the Berkshires
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
8.8 out of 10, Excellent, (41)
"Springs Motel has a one of a kind vibe, loved the Double bed room! & managed by experienced, friendly people. Can’t wait to book a cabin next time with my family !! "
The price is AED 391
AED 429 total
includes taxes & fees
20 Apr - 21 Apr
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
20 Apr - 21 Apr
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

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, (1798)
"The location to jimney peak was great."
The price is AED 380
AED 458 total
includes taxes & fees
23 Apr - 24 Apr
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, (927)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 550 total
includes taxes & fees
21 Apr - 22 Apr
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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 960 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 Lenox is located 12.2 mi (19.6 km) from the heart of Cheshire. Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Maple Terrace Motel: A seasonal outdoor pool along with freebies like breakfast, WiFi, and parking are available during your stay. Central Cheshire is 10.2 mi (16.4 km) away. The Villager Motel: Enjoy the in-room free WiFi, and freebies including breakfast and parking. Located 12.3 mi (19.9 km) from the heart of Cheshire. Berkshire Inn: Central Cheshire is 9.6 mi (15.5 km) away. A seasonal outdoor pool and free WiFi are available during your stay, along with room amenities like a microwave. Williamstown Motel: 9.8 mi (15.8 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 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.