Find Cheshire motels from $55

If you can’t find a motel in Cheshire, let Expedia help you find a motel or something similar from over 888 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.

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.

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. Willows Motel Williamstown: A library along with freebies like breakfast, WiFi, and parking are available during your stay. Central Cheshire is 10.1 mi (16.2 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. 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. Pleasant Valley Motel West Stockbridge: 19.2 mi (30.9 km) from the heart of Cheshire. Enjoy access to the free WiFi and free parking, as well as room amenities like a microwave.

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, Brodie Mountain, and Jiminy Peak Mountain Resort.

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, April, March, and February, with each month seeing an average of 8 inches of snowfall.

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.