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Hotels in Chesterfield

Choose from 513 Chesterfield Hotel Deals

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. ...
9.4/10 Exceptional! (2,215 reviews)
We received a warm welcome Waited just a few minutes for room to be ready Breakfast included with stay which is always a plus to get you on your way Enough parking for all

Reviewed on Mar 2, 2026

D. Hotel Suites & Spa
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! (867 reviews)
Love it here. We stay a few times a year and are actually local to the hotel. Just a relaxed experience.

Reviewed on Mar 1, 2026

Berkshire Mountain Lodge
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
400 Russell St Hadley MA
  • 6 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,006 reviews)
This is an excellent place to stay while in the Amherst/Hadley area. Convenient location, a friendly and welcoming team of staff, a complimentary breakfast (with some healthy options available) served every morning, a swimming pool, and plenty of space, both in the guest rooms as well as in the common ...

Reviewed on Mar 3, 2026

Comfort Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
  • 9 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,002 reviews)
Fair. Pool was closed. Everything under construction. Poor location.

Reviewed on Mar 1, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
  • 45 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
9.2/10 Wonderful! (606 reviews)
Stayed here because I was having the floors in my house redone everything was clean crispy everything worked no problems with that but I don’t know if there was a generator or the heating air ducts that were allowed enough that I left the TV on at night and the TV must collect some kind of satellite ...

Reviewed on Mar 2, 2026

Courtyard by Marriott West Springfield
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! (1,006 reviews)
The first night was awful loud couldn’t sleep the people next door and across , had to sleep with my tv on 60 and still could hear at times paid for a tub accessible room and I thought when u pay to hold a room that’s the point but on the day of got a call that room wasn’t available, this was a staycation ...

Reviewed on Mar 3, 2026

Tru by Hilton Chicopee Springfield
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 room service. Our guests praise the helpful staff in our reviews. Popular attractions Mullins ...
8.8/10 Excellent! (1,002 reviews)
Staff was wonderful! The room was very clean!

Reviewed on Mar 1, 2026

Hotel UMass
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
  • 12 min drive from Chesterfield Gorge
Stay at this hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (977 reviews)
Was an absolute awesome stay. Got a upgrade without asking. Room was extremely clean. Walked everywhere.

Reviewed on Mar 1, 2026

The Ellery
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! (1,002 reviews)
The door to my room was broken. "Just throw your weight into it," should not be the instructions from hotel staff. The handle/latch had been troublesome for a while, judging by the instructions on the handle (on this room only) to pull up on the handle, not down, to open the door. I made so much ...

Reviewed on Feb 23, 2026

Red Roof Inn PLUS+ South Deerfield – Amherst
Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

3 out of 5
423 Russell St Hadley MA
  • 6 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Hadley. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (700 reviews)
Great service

Reviewed on Mar 2, 2026

Courtyard by Marriott Hadley Amherst
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

3 out of 5
115A Conz Street 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 in our reviews. ...
9.2/10 Wonderful! (1,003 reviews)
Super friendly staff, easy checkout, very quiet, good continental breakfast and a variety of "on the go" snacks you could grab

Reviewed on Mar 3, 2026

Fairfield Inn & Suites Springfield Northampton/Amherst
Inn on Boltwood

Inn on Boltwood

3 out of 5
30 Boltwood Ave. Amherst MA
  • 4 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Amherst. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (772 reviews)
Lovely stay!

Reviewed on Mar 2, 2026

Inn on Boltwood
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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Frequently Asked Questions About Chesterfield hotels

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How many hotels are there in Chesterfield?

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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.