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Hotels in Chesterfield

Choose from 514 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! (2,223 reviews)
We spent a weekend at this hotel. To be honest, I think I was expecting a little better based on the strong reviews. The property was in decent shape but the rooms were incredibly sparse and basic: our bathroom shower curtain liner fell off repeatedly, no ventilation in there, room furniture was ...

Reviewed on Mar 24, 2026

D. Hotel Suites & Spa
Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

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! (1,007 reviews)
N/A

Reviewed on Mar 23, 2026

Comfort Inn & Suites Hadley - Amherst
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! (885 reviews)
very clean and friendly staff

Reviewed on Mar 24, 2026

Berkshire Mountain Lodge
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 MGM Springfield ...
9.6/10 Exceptional! (166 reviews)
Sketchy pulling in, old abandon place in front.

Reviewed on Mar 21, 2026

Blue – A Modern Hotel, an Ascend Collection Hotel
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! (1,000 reviews)
Staff was pleasant! Clean and the restaurant was excellent!

Reviewed on Mar 22, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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)
Excellent service.

Reviewed on Mar 24, 2026

Fairfield Inn & Suites Springfield Northampton/Amherst
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! (1,001 reviews)
Clean, friendly staff, quiet comfortable room and just enough breakfast to start my day. The stay worked out perfectly between travels.

Reviewed on Mar 25, 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! (1,000 reviews)
Such a zen and peaceful place Just what I needed I’ll be back for sure And the staff are excellent also

Reviewed on Mar 24, 2026

Tru by Hilton Chicopee Springfield
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! (704 reviews)
Clean room. No conditioner in the shower and soap almost out.

Reviewed on Mar 23, 2026

Courtyard by Marriott Hadley 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! (1,004 reviews)
It’s ok.

Reviewed on Mar 24, 2026

Red Roof Inn PLUS+ South Deerfield – Amherst
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 out of 5
572 Riverdale St West Springfield MA
  • 46 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. Our guests praise the helpful staff ...
8.4/10 Very Good! (854 reviews)
The staff is friendly and helpful.

Reviewed on Mar 23, 2026

Candlewood Suites West Springfield by IHG
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! (780 reviews)
great location and charm

Reviewed on Mar 19, 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

Where can I find the best last-minute travel deals?

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How many hotels are there in Chesterfield?

With over 514 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 $95.

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.