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Hotels in Chesterfield

Choose from 487 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! (2,243 reviews)
Everything was perfect.

Reviewed on Dec 17, 2025

D. Hotel Suites & Spa
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! (993 reviews)
N/a

Reviewed on Dec 20, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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! (1,002 reviews)
Room was clean and smelled fine.

Reviewed on Nov 30, 2025

Quality Inn West Springfield
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! (585 reviews)
The hotel was conveniently located, as my child was doing a camp over at Springfield College and we didn’t want to stay right in the city. The room was clean and staff were friendly. The only thing we would have appreciated better would have been breakfast included.

Reviewed on Dec 14, 2025

Courtyard by Marriott 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! (793 reviews)
Spacious room and loved pool and hot tub!

Reviewed on Dec 19, 2025

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! (1,004 reviews)
There was blood strains on the bedding.

Reviewed on Dec 20, 2025

Comfort Inn & Suites
Riverdale Inn

Riverdale Inn

2 out of 5
1500 Riverdale Street West Springfield MA
  • 42 min drive from Chesterfield Gorge
Stay at this motel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions MGM Springfield and Olympia Ice Center are ...
5.8/10 (999 reviews)
Everything was wonderful and I will be staying here again.

Reviewed on Nov 28, 2025

Riverdale Inn
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

2.5 out of 5
2 Southampton Rd Westfield MA
  • 42 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Westfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (902 reviews)
Stayed one night had no problems

Reviewed on Nov 30, 2025

Quality Inn Westfield - 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! (1,001 reviews)
They put a hold on my room for incidentals and never gave the money back to me. That charged me the hold! Terrible way to do business, don’t hide fees from your customers.

Reviewed on Dec 16, 2025

Red Roof Inn PLUS+ South Deerfield – Amherst
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 ...
9.4/10 Exceptional! (109 reviews)
New and still working some kinks out but overall a great stay.

Reviewed on Dec 18, 2025

Blue – A Modern Hotel, an Ascend Collection Hotel
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 ...
9/10 Wonderful! (1,000 reviews)
Great, gracious hotel with old time charm. Clean and comfortable too.

Reviewed on Dec 20, 2025

Hotel Northampton
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 out of 5
1011 Riverdale St West Springfield MA
  • 44 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in West Springfield. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,000 reviews)
Yes it was clean

Reviewed on Dec 13, 2025

Hampton Inn West Springfield
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 487 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 $90.

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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.