Search Motels in Chester

If you’re having a hard time finding motels in Chester, let Expedia help you find a motel or something similar from over 794 lodging options in the larger area. Just use our search tools to filter by price per night or cost-saving amenities such as free parking and free airport transportation.

When you stay at a motel, you’ll often find an outdoor pool and free parking. With a stay at a motel, you’ll usually access your room directly from the parking lot. Starting in the early 1950s, customized neon signs often lit up the roadside motels, and you can see these today along the historic U.S. Route 66.

These are some of our customers’ favorite motels to book in the larger area. The Little Lion is located 18.4 mi (29.6 km) from the heart of Chester. Enjoy access to the picnic area, and freebies including WiFi and parking. FairBridge Inn Express: Free WiFi and free parking are available during your stay, along with room amenities like a microwave. Central Chester is 17.4 mi (28 km) away. Monument Mountain Motel: Enjoy access to the picnic area, and freebies including WiFi and parking. Located 19.5 mi (31.4 km) from the heart of Chester. Berkshire Inn: Central Chester is 18.4 mi (29.6 km) away. A seasonal outdoor pool and free WiFi are available during your stay, along with room amenities like a microwave. Howard Johnson by Wyndham Lenox: 17 mi (27.3 km) from the heart of Chester. Enjoy access to the 24-hour front desk, and freebies including WiFi and parking.

Some outdoorsy places nearby include Glendale Falls, Iroquis Waterfront, and Pyramid Lake. You’ll find these family-friendly sights in the area: Bousquet Ski Area, Berkshire Museum, and Berkshire Scenic Railway Museum. While you’re checking out the area, consider visiting Chester Town Hall, Blandford Ski Area, and Jacob’s Pillow.

Weather can make or break a roadtrip, so here’s some data about year-round temperatures in Chester to help you plan yours: The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

We’ve gathered some information about getting around Chester to help you navigate your stay: Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the city center. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.