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Hotels in Chesterfield

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Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
  • 43 min drive from Chesterfield Gorge
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,008 reviews)
"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

Quality Inn West Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
  • 24 min walk from Chesterfield Gorge
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,005 reviews)
"Friendly staff, great coffee and very clean ."

Reviewed on Jul 1, 2026

Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
  • 20 min drive from Chesterfield Gorge
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,154 reviews)
"They have an onsite gym but it doesn’t open until 8am, so wasn’t able to access it before leaving for work commitments. Breakfast was the low point, pretty greasy and unappetizing. Nowhere to sit even if the table were unoccupied as they were so sticky and dirty. The rest of the hotel was spotless ..."

Reviewed on Jul 1, 2026

D. Hotel Suites & Spa
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
  • 10 min walk from Chesterfield Gorge
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and 5 coffee shops/cafes. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (1,006 reviews)
"Convenience."

Reviewed on Jul 1, 2026

Hotel UMass
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

2.5 out of 5
117 Conz St Northampton MA
  • 14 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,001 reviews)
"I am pretty sure people live here full time."

Reviewed on Jul 1, 2026

Quality Inn & Suites Northampton - Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd South Deerfield MA
  • 13 min drive from Chesterfield Gorge
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
7.2/10 Good! (1,005 reviews)
"Was surprisingly very clean!!"

Reviewed on Jul 1, 2026

Red Roof Inn PLUS+ South Deerfield – Amherst
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
  • 12 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,008 reviews)
"We love staying at the Ellery. The location is conveniently close to the center of Northampton, the staff is always welcoming and helpful, and always-available cookies and tea make the place feel cozy and homey."

Reviewed on Jul 2, 2026

The Ellery
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
  • 38 min drive from Chesterfield Gorge
Stay at this hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9/10 Wonderful! (1,002 reviews)
"I really like the set up of the rooms in a Tru Hilton hotel. Beds are great, bathroom is great, hooks on the wall, a pull out desk so you can watch tv. Heating and cooling system works well. Great hotel."

Reviewed on Jul 2, 2026

Tru by Hilton Chicopee Springfield
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
  • 44 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Big E and MGM ...
9.4/10 Exceptional! (234 reviews)
"Nice clean and bright room that was well appointed. Don’t let the location affect your choice to stay at this property. It was peaceful and a terrific stay in every way!"

Reviewed on Jun 30, 2026

Blue – A Modern Hotel, an Ascend Collection Hotel
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street West Springfield MA
  • 43 min drive from Chesterfield Gorge
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
7/10 Good! (1,001 reviews)
"I havr nothing to complain about"

Reviewed on Jul 1, 2026

Red Roof Inn PLUS+ West Springfield
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
  • 18 min walk from Chesterfield Gorge
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
9.4/10 Exceptional! (118 reviews)
"alls well"

Reviewed on Jun 29, 2026

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
  • 13 min drive from Chesterfield Gorge
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,001 reviews)
"Absolutely the most beautiful hotel I ever stayed in!"

Reviewed on Jun 30, 2026

Hotel Northampton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find cheap hotels in Chesterfield

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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chesterfield.

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 509 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $106. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chesterfield hotel deals at the last minute.

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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 509 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 $106.

How to find cheap car rentals in Chesterfield?

Finding a cheap car rental deal in Chesterfield is as easy as scoring cheap hotels in Chesterfield. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.