Book Hotels in Chesterfield, MA
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Top Chesterfield hotels

Blue – A Modern Hotel, an Ascend Collection Hotel
"Great hotel, exquisite decor, very clean, massage chair in room… Enjoyed the experience."
Reviewed on Jun 27, 2026

D. Hotel Suites & Spa
"Great location for graduation weekend."
Reviewed on Jun 29, 2026

The Ellery
"Friendly staff and unique, nice things like real dishware at breakfast and some unusual options at breakfast such as avocado and a variety of toppings for avocado toast. Also, very good coffee which was also a lovely find. Be aware, though, that The Ellery is a motel and is somewhat upscale but not ..."
Reviewed on Jun 29, 2026

Berkshire Mountain Lodge
"Great hotel"
Reviewed on Jun 29, 2026

Tru by Hilton Chicopee Springfield
"👌"
Reviewed on Jun 28, 2026

Hotel UMass
"good"
Reviewed on Jun 29, 2026

Quality Inn & Suites Northampton - Amherst
"Very disappointing experience. The room rate soared from $160 on Thursday night to $459 and $519 for Friday/Saturday. Based on the quality of the property this seems to be excessive. The cable TV service did not work for our entire stay. The night desk manager Nicole was very nice and acknowledged ..."
Reviewed on Jun 29, 2026

Red Roof Inn PLUS+ South Deerfield – Amherst
"Hotel was old and rundown as expected. Room was incredibly humid and smelled. Bathroom had no fan so everytime someone showered the room became even more humid. We came back on our second day and all our clothes in our suitcase were moist. We were there for a kids sports tournament so everything ..."
Reviewed on Jun 28, 2026

Quality Inn West Springfield
"La chambre n'était pas très propre, draps tâché, les vitres et balcon était vraiment salle, il y avait de la moisissure dans la salle de bain, le mobilier était usé. Et la salle à déjeuner fesait vraiment dur."
Reviewed on Jun 28, 2026
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

Berkshire Mountain Lodge
"The room was attractive and clean - and the staff were extremely helpful and friendly. The room was also fairly inexpensive and a quick drive into Lenox. All the rooms were full suites with kitchens and living rooms. This was nice, but we didn't really need the kitchen and would have preferred an on-site restaurant for breakfast. Still, the super friendly staff directed us to the nearby Electra's cafe which had the best French toast I have ever eaten. We would definitely stay there again."
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