Find Pittsfield motels from $109

If you’re having a hard time finding motels in Pittsfield, expand your search to find motels in the surrounding area or let us help you find a similar property from more than 31 hotels and other lodging options. Simply use our search tools to filter by price per night or cost-saving amenities such as free parking and free airport transportation.

At most motels, you’ll often find an outdoor pool and free parking. When you stay at a motel, you’ll usually access your room from an outside corridor overlooking the parking lot. In the U.S., motels became more commonplace at the end of the 1940s with the appeal of road trip vacations, peaking in the mid-1960s with more than 60,000 properties.

Here you’ll find some of Expedia customers’ favorite motels in the larger area. Sleep Woodstock Motel is located 16.1 mi (26 km) from the heart of Pittsfield. Enjoy access to the picnic area, and freebies including WiFi and parking. Middlebury Sweets Motel: Free WiFi and free parking are available during your stay, along with room amenities like a private yard. Central Pittsfield is 22.2 mi (35.8 km) away. Happy Bear Motel: Enjoy access to the free WiFi and free parking, as well as room amenities like a microwave. Located 8.7 mi (14 km) from the heart of Pittsfield. Rodeway Inn Rutland: Central Pittsfield is 13.2 mi (21.3 km) away. A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. Econo Lodge Rutland City near Hwy 7: 14.7 mi (23.6 km) from the heart of Pittsfield. Enjoy access to the business center, and freebies including breakfast, WiFi, and parking.

Some outdoorsy places nearby include Gifford Woods State Park, Killington Peak, and Green Mountain National Forest. You’ll find these family-friendly sights in the area: Killington Adventure Center, Black Dog Sports, and Hathaway Farm. While you’re checking out the area, consider visiting Appalachian Trail Adventures, Green Mountain National Golf Course, and Pico Mountain at Killington Ski Resort.

Weather can make or break a roadtrip, so we’ve gathered some data about year-round temperatures in Pittsfield 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 23°F. The snowiest months in Pittsfield are January, March, February, and April, with each month seeing an average of 10 inches of snowfall.

We’ve gathered some information about getting around Pittsfield to help you navigate your stay: Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the city center. Otherwise, you can search for flights to Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you’d like to explore around the area, you may want a rental car for your journey.