Book Hotels in Chesterfield, MA
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Top Chesterfield hotels
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
"Having the pool and hot tub was great. Very clean. Breakfast was complete with oatmeal and hot breakfast choices. Location was Central to all sites like Tanglewood. Highly recommended."
Reviewed on Aug 18, 2026
Berkshire Mountain Lodge
"The rooms were spotless and a good size. And is not far from Lenox which was our focus. I’d suggest that guests bring some food with them and there is a supermarket nearby. There is not a morsel of food in the ‘resort’. The tv is complicated and I’m not sure why it is set up the way it is. Check ..."
Reviewed on Aug 17, 2026
Hotel UMass
"The property is beautiful, well kept, and clean. It is difficult to find the place because it is in the middle of UMASS campus. The signage needs improvement. It is a long walk from the parking lot to the lobby. Once you have the location and parking figure out, the place is great."
Reviewed on Aug 18, 2026
Quality Inn West Springfield
"The pool was closed, and then kinda smelled super strong from the shock. But the screen thingy could have been opened more. Also the remote tv situation didn’t work, which was a pain but we weren’t in the room much. Also the breakfast room is stuffy and crowded and it’s not a good set up. But breakfast ..."
Reviewed on Aug 17, 2026
FairBridge Inn Express
"I called to check that it was alright if I arrived after 10:30 PM. I was told no problem. When I arrived the front door was locked, no one answered the buzzer. When I called, I was told that someone would be right there. 7 or 8 minutes later, I called again and asked how long it would be. Should ..."
Reviewed on Aug 18, 2026
D. Hotel Suites & Spa
Hotel Northampton
Blue A Modern Hotel, an Ascend Collection Hotel
Red Roof Inn PLUS+ West Springfield
Chesterfield Hotel & Travel Guide\n
Do you want to have an adventure in Chesterfield? We suggest you secure accommodations as soon as you know your itinerary, as there's only 1 option within an easy driving distance of the main center of Chesterfield.
The Inn Nature Bed & Breakfast is the nearest room to the heart of Chesterfield and it is merely a brief drive away.
The Hotel Northampton is about 12 miles (20 kilometers) away from central Chesterfield. Another place to stay is the Naomi's Inn Bed & Breakfast, which is approximately 20 miles (36 kilometers) away. The Residence Inn by Marriott West Springfield and also the Hampton Inn & Suites Greenfield are two more Travelocity-listed accommodation options worth looking into around Chesterfield.
Making plans to get a little out of the center? Western Massachusetts offers many attractions. Admire the terrain of Western Massachusetts's mountains. In addition, you should explore a selection of the area's history museums. Enlightened travelers in this pocket of United States of America love skiing.
The nearest accommodation options in Franklin County include Deerfield and Bernardston. Deerfield is 17 miles (27 kilometers) to the northeast of Chesterfield, while Bernardston is 25 miles (42 kilometers) to the northeast. Travelocity-registered room options in Deerfield include the Days Inn Greenfield and Rodeway Inn. The The Log Cabin Bed & Breakfast and The Inn At Crumpin Fox are amongst the Travelocity-registered hotels and apartments in Bernardston.
Get yourself a sports fix by making the trek to Times Union Center, which you will find 50 miles (79 kilometers) to the west of Chesterfield. Those that need to find Travelocity-listed accommodation options in the area surrounding the stadium can select from the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.
When you're flying via Bradley International Airport and choose to base yourself nearby, try Sheraton Hartford Hotel at Bradley Airport or Holiday Inn Express & Suites Bradley Airport.
Frequently asked questions
Recent Chesterfield hotel reviews by fellow wanderers
Inn on Boltwood
"If you like old inns with modern amenities in historic places , this is your place. The beds are comfortable, the restaurant is first rate for breakfast or dinner, and there's a lovely, spacious library with a fireplace for reading or conversation with friends. The front desk staff are universally friendly and helpful, and provide an unlimited number of bottles of Saratoga water, on request. The inn is located alongside a leafy quad that reduces noise from Amherst's main road. Given the inn's age, a guest might experience noise from heavy-footed guests in the room above, but we did not. Noise was not an issue."
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