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Berkshire Mountain Lodge
"The hotel is as described. However they hold $150 for the incidentals fee. That seems extremely large. Especially with no restaurant on premise. Otherwise it's a fine hotel."
Reviewed on Jul 22, 2026
D. Hotel Suites & Spa
"Hot tub: Control to turn on the jets didn't work. Water was tepid, not hot."
Reviewed on Jul 22, 2026
Hotel Northampton
Quality Inn West Springfield
Blue – A Modern Hotel, an Ascend Collection Hotel
"Our stay at this hotel was wonderful. The staff here are so professional, friendly, and attentive. It gave calm vibes with a comfy area to hang out, play pool, snack on freshly baked cookies, and hot beverages ready to go when needed. We would book again in a heartbeat!"
Reviewed on Jul 22, 2026
Hotel UMass
"This rooms were very clean and spacious and the staff were friendly. Breakfast was good and the parking was very convenient"
Reviewed on Jul 21, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
"The Holiday Inn Express Pittsfield-Lenox is a new (opened 10/25) lower cost hotel in the heart of the Berkshires, close to Tanglewood, Shakespeare and Company, The Berkshire Stage and most of the art and culture opportunities offered by the Berkshires. It is clean, the complementary hot breakfast ..."
Reviewed on Jul 22, 2026
FairBridge Inn Express
Red Roof Inn PLUS+ South Deerfield – Amherst
The Ellery
Comfort Inn & Suites Hadley - Amherst
"I was very pleasantly surprised at this hotel. I booked it because my usual hotels were full. It’s a bit lower level than I usually choose for a hotel but wow was it ever nice!! Lovely rooms and lobby area. Comfortable beds. Great breakfast. Changed my assumptions about the Comfort Inn entirely!"
Reviewed on Jul 23, 2026
Red Roof Inn PLUS+ West Springfield
Find cheap hotels in Chesterfield
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Choosing the right hotel in Massachusetts has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chesterfield’s 506 hotels. Choose the one that best catches your trip’s tourist drift.
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Frequently Asked Questions About Chesterfield hotels
Where can I find the best last-minute travel deals?
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How many hotels are there in Chesterfield?
With over 506 hotels in Chesterfield, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $77.
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