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Hotels in Chesterfield

Choose from 457 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
Stay at this 3-star 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! (2,270 reviews)
"Property has character and has its excellent adjacent restaurant. Service staff is welcoming and accommodating. Some furniture is not just old but worn. Breakfast room could be brightened."

Reviewed on Jul 13, 2025

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 room service. Our guests praise the helpful staff in our reviews. Popular attractions Mullins ...
8.6/10 Excellent! (1,011 reviews)
"Great place to stay while spending time with your UMASS student! Easy parking, great location, friendly staff"

Reviewed on Jul 13, 2025

Hotel UMass
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! (1,007 reviews)
"Safe and convenient"

Reviewed on Jul 11, 2025

Quality Inn West Springfield
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! (1,005 reviews)
"This place was lovely. Staff was friendly. Room was perfect. Loved hanging out on the patio on the warm day. I would definitely come back here when visiting our family and friends."

Reviewed on Jul 7, 2025

Comfort Inn & Suites
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! (1,002 reviews)
"Garbage can could be moved so not by door. Kind of in the way as you are trying to get into door and always over flowing with stinky garbage and cigarettes."

Reviewed on Jul 3, 2025

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 (1,000 reviews)
"One my favorite plac"

Reviewed on Jul 7, 2025

Red Roof Inn PLUS+ 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 ...
8.8/10 Excellent! (1,004 reviews)
On the way to Maine
"Checking in was fast and easy. The room was small but adequate for an overnight stay. CLEAN which is most important to me. The outdoor area was nice to sit outside. Staff was friendly. Would recommend."

Reviewed on Jul 10, 2025

Tru by Hilton Chicopee Springfield
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
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (818 reviews)
"Clean but needs renovations"

Reviewed on Jul 8, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express
FairBridge Inn Express
2.5 out of 5
16 Cheshire Road, Pittsfield, MA
  • 12 min drive from Chesterfield Gorge
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (739 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."

Reviewed on Jul 1, 2025

FairBridge Inn Express
Riverdale Inn
Riverdale Inn
2 out of 5
1500 Riverdale Street, On Route 5, 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 Big E and MGM Springfield are located ...
5.8/10 (1,007 reviews)
"Close to shopping area, nice to stay and services."

Reviewed on Jul 10, 2025

Riverdale Inn
Hotel Northampton
Hotel Northampton
3.5 out of 5
36 King Street, Northampton, MA
  • 13 min drive from Chesterfield Gorge
Stay at this 3.5-star 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! (1,002 reviews)
"Beautiful historic building, there was a wedding party the night we stayed but we were in a 5th floor room and heard nothing. Lots of fun dining options within a couple blocks."

Reviewed on Jul 6, 2025

Hotel Northampton
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 ...
7/10 Good! (1,002 reviews)
"My name is Ray Omar is pretty good"

Reviewed on Jul 5, 2025

Quality Inn & Suites Northampton - Amherst
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 457 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 $88. 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 457 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 $88.

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.