Search for Cheap Deals on
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. ...
9.2/10 Wonderful! (2,225 reviews)
This has become our company's preferred hotel for business trips to the Holyoke/Northampton area. It is clean, quiet, safe, convenient, and the breakfast is stellar.

Reviewed on Mar 10, 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! (871 reviews)
the room was huge - we loved it!!

Reviewed on Mar 11, 2026

Berkshire Mountain Lodge
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! (1,013 reviews)
Beautiful view from rooftop pool

Reviewed on Mar 8, 2026

Comfort Inn & Suites Hadley - Amherst
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 ...
9.2/10 Wonderful! (607 reviews)
Clean and efficient. Great location to find a meal and get away from the Big E chaos.

Reviewed on Mar 9, 2026

Courtyard by Marriott West 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
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)
Hotel is going through a renovation which makes the place a little rougher than it’s used to be. No parking or limited parking at entrance of hotel. Valet parking personnel were parking cars on entrance round entrance and in the mourning, they were towing those cars from the property. Not a good ...

Reviewed on Mar 8, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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)
The property was clean but the beds were very uncomfortable. They need to replace the mattresses.

Reviewed on Mar 9, 2026

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 ...
9.6/10 Exceptional! (160 reviews)
Highly recommend this was a beautiful hotel. The rooms were beautiful. The staff were so nice and I was so excited when I walked into the room and there was a massage chair.

Reviewed on Mar 9, 2026

Blue – A Modern Hotel, an Ascend Collection Hotel
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! (985 reviews)
The Ellery is a super comfortable simple and friendly hotel. It is ideal to visit your students at Smith College.

Reviewed on Mar 9, 2026

The Ellery
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 booked because of the pool however pool was out of service my entire stay and I was unable to use, def a let down

Reviewed on Mar 6, 2026

Fairfield Inn & Suites Springfield Northampton/Amherst
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! (1,001 reviews)
The only problem I have with this hotel is the bed is too hard I didn’t make it through the night I had to go home

Reviewed on Mar 7, 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! (701 reviews)
Great service

Reviewed on Mar 2, 2026

Courtyard by Marriott Hadley Amherst
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 ...
8.8/10 Excellent! (1,004 reviews)
The staff was very helpful and professional. The room was very clean and had a great view. We would stay there again!

Reviewed on Mar 7, 2026

Hotel UMass
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 514 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 $95. 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 $95.

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.