Search for Cheap Deals on
Hotels in Chesterfield

Choose from 507 Chesterfield Hotel Deals

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! (973 reviews)
"Staff, breakfast, spaciousness of the room, all fabulous."

Reviewed on Jun 11, 2026

Berkshire Mountain Lodge
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 5 coffee shops/cafes. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (1,021 reviews)
"The parking situation was unacceptable when we arrived. The garage was closed and the lady preventing people from entering was very unhelpful. As an out of town visitor, I had no idea where she expected me to park. I had bags and I was told to park in the circle to drop them off. It was still quite ..."

Reviewed on Jun 10, 2026

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! (1,011 reviews)
"Absolutely the worst night ever. I stayed to get rest the night before an important meeting and not at all good. First Place once u get off elevator is filthy, wallpaper peeling and Ac actually had moldy dust. Hair eminent in shower !! Sound proof rooms !!! No way. Young women room in next room was ..."

Reviewed on Jun 11, 2026

Quality Inn West Springfield
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! (2,206 reviews)
"Nice outdoor part of the restaurant for dinner. Good drinks and atmosphere."

Reviewed on Jun 10, 2026

D. Hotel Suites & Spa
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! (1,012 reviews)
"Pool is close and I wasn't aware until after I did check in... and no discount were offer for inconvenience"

Reviewed on Jun 9, 2026

Tru by Hilton Chicopee Springfield
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
  • 12 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 breakfast and the helpful ...
9.2/10 Wonderful! (1,013 reviews)
"Very nice, clean, love the parking. Great hotel"

Reviewed on Jun 10, 2026

The Ellery
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 Big E and MGM ...
9.4/10 Exceptional! (216 reviews)
"Blue was very nice kept and staff specially Dax were super helpful. The massage chair in the room is really great. It is centrally located with restaurants near by and easy access to downtown."

Reviewed on Jun 10, 2026

Blue – A Modern Hotel, an Ascend Collection Hotel
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! (1,009 reviews)
"Bugs in the room were a turnoff."

Reviewed on Jun 10, 2026

Red Roof Inn PLUS+ South Deerfield – Amherst
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 ...
9.4/10 Exceptional! (1,008 reviews)
"Fairly clean room; front desk promptly responded to a plumbing issue in my room."

Reviewed on Jun 8, 2026

Comfort Inn & Suites Hadley - 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! (888 reviews)
"Had a nice evening . Thank you.."

Reviewed on Jun 11, 2026

Candlewood Suites West Springfield by IHG
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 Big E and MGM Springfield are located ...
6/10 (1,003 reviews)
"Needs updates but if ur just swinging in and need a quick place to rest its fine staff is sweet"

Reviewed on Jun 10, 2026

Riverdale Inn
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
  • 18 min walk from Chesterfield Gorge
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
9.4/10 Exceptional! (102 reviews)
"Room was very clean and staff went far a beyond to accommodate my husbands needs."

Reviewed on Jun 9, 2026

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Chesterfield hotel with Hotwire to complete your one-of-a-kind travel checklist.

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 507 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 $102. 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.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chesterfield. No matter your reason for visiting Chesterfield, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Chesterfield hotels

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

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chesterfield for as low as $102.

How many hotels are there in Chesterfield?

With over 507 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 $102.

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.