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Hotels in Chesterfield

Choose from 508 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. ...
9.2/10 Wonderful! (2,232 reviews)
Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back

Reviewed on Jan 31, 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! (824 reviews)
What a great find! Fantastic accommodations with great customer service. My kids asked if they could take the pull out couch home with them it was so comfy. We enjoyed the pool and hot tub. The staff graciously allowed us a late checkout and the maintenance and grounds crew was impressive. They kept ...

Reviewed on Jan 31, 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! (1,003 reviews)
Clean room, friendly staff,

Reviewed on Feb 1, 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! (1,001 reviews)
generally good

Reviewed on Jan 19, 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 ...
9/10 Wonderful! (596 reviews)
Clean, great area, and welcoming.

Reviewed on Jan 8, 2026

Courtyard by Marriott West Springfield
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 ...
9/10 Wonderful! (957 reviews)
clean room, nice staff

Reviewed on Jan 31, 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 ...
8.8/10 Excellent! (1,001 reviews)
The room was beautiful spotless I am picky

Reviewed on Jan 28, 2026

Tru by Hilton Chicopee Springfield
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 ...
7/10 Good! (1,003 reviews)
All good. Strange stay as there was a large storm approaching.

Reviewed on Jan 30, 2026

Red Roof Inn PLUS+ South Deerfield – Amherst
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 ...
6.8/10 (1,003 reviews)
The beds were super comfortable and the staff was really nice. The rooms were a bit dingy, looked like the chair had never been vacuumed off ever and like they don’t move anything when they vacuum or sweep. The water pressure was really good and nice hot water. Ceiling fan did not work but that was ...

Reviewed on Jan 28, 2026

Red Roof Inn PLUS+ West Springfield
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! (1,005 reviews)
I don’t know the younger man’s name, but he remembered me from my stay over a year ago, and was so kind welcoming me back! The rooms are clean, the location is fantastic! Walking distance to some of my favourite places in Northamption!

Reviewed on Jan 23, 2026

Fairfield Inn & Suites Springfield Northampton/Amherst
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
  • 10 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (821 reviews)
Great staff, beautiful hotel. Would definitely recommend

Reviewed on Jan 27, 2026

Hotel On North
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. ...
9.2/10 Wonderful! (762 reviews)
Great stay. Convenient location on the edge of campus in town. Comfortable room. Friendly staff. Free parking. Excellent dinner at 30Boltwood. Highly recommend!

Reviewed on Feb 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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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 508 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 $97. 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 508 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 $97.

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.