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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

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, (698)
"Stay was good as usual, other than a single person hanging out on balcony pacing back and forth making it uncomfortable room was clean other than food found left in microwave. Overall have had good stays and would keep booking"
The price is SAR 259
SAR 289 total
includes taxes & fees
28 Jan - 29 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 SAR 259
SAR 289 total
includes taxes & fees
28 Jan - 29 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, (707)
"The room was clean, and the staff was helpful and friendly. The location was great, and parking was convenient. However, the bathroom was extremely disappointing. There were stains and hairs on the toilet seat, and the overall cleanliness was far below acceptable standards."
The price is SAR 296
SAR 331 total
includes taxes & fees
28 Jan - 29 Jan
Howard Johnson by Wyndham Lenox
Willows Motel Williamstown
Room

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (896)
"Great weekend away in Williamstown. Very convenient to town, excellent value and the owner is exceptionally nice. "
The price is SAR 319
SAR 356 total
includes taxes & fees
28 Jan - 29 Jan
Willows Motel Williamstown
Cozy Corner Motel
Room

Cozy Corner Motel

2.0 star property
9.0 out of 10, Wonderful, (783)
"Property is on the crappy end of town but the river is between your hotel and that neighborhood. I definately recommend staying at this hotel"
The price is SAR 278
SAR 328 total
includes taxes & fees
2 Feb - 3 Feb
Cozy Corner Motel
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (761)
"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 360 total
includes taxes & fees
28 Jan - 29 Jan
Berkshire Inn
Blue Vista Motor Lodge
Front of property

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (161)
"Clean. Quiet"
The price is SAR 532
SAR 562 total
includes taxes & fees
28 Jan - 29 Jan
Blue Vista Motor Lodge
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (959)
"The room and bathroom were very clean. "
The price is SAR 221
SAR 243 total
includes taxes & fees
31 Jan - 1 Feb
Pleasant Valley Motel West Stockbridge
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 Jan - 29 Jan
Wagon Wheel Inn
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (583)
"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 259
SAR 289 total
includes taxes & fees
28 Jan - 29 Jan
Econo Lodge Lee - Great Barrington
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (542)
"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 SAR 353
SAR 394 total
includes taxes & fees
28 Jan - 29 Jan
Maple Terrace Motel
Berkshire Travel Lodge
Exterior

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (392)
"Safe and friendly "
The price is SAR 246
SAR 266 total
includes taxes & fees
9 Feb - 10 Feb
Berkshire Travel Lodge
Howard Johnson by Wyndham Williamstown
Exterior

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (831)
"The room was very large and clean."
The price is SAR 360
SAR 402 total
includes taxes & fees
30 Jan - 31 Jan
Howard Johnson by Wyndham Williamstown
Heart of the Berkshires
Front of property

Heart of the Berkshires

9.4 out of 10, Exceptional, (3)
"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 SAR 279
SAR 366 total
includes taxes & fees
28 Jan - 29 Jan
Heart of the Berkshires
Williamstown Motel
Front of property

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (252)
"Very helpful, friendly, and attentive owners"
The price is SAR 371
SAR 415 total
includes taxes & fees
29 Jan - 30 Jan
Williamstown Motel
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 SAR 291
SAR 325 total
includes taxes & fees
28 Jan - 29 Jan
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
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. "
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, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is SAR 563
SAR 655 total
includes taxes & fees
30 Jan - 31 Jan
Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is SAR 867
SAR 969 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (235)
"Absolutely wonderful. Charming, pristine and cozy for an overnight stay. "
The price is SAR 563
SAR 855 total
includes taxes & fees
28 Jan - 29 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 941 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. 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. 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. Howard Johnson by Wyndham Lenox: Central Cheshire is 12.2 mi (19.6 km) away. Free WiFi and free parking are available during your stay, along with room amenities like a soaking tub. 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 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.