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Hotels in Chesterfield

Last Minute Hot Rate® Hotel Deals in Chesterfield

We Hide Hotel Names So You Can Find 4-Star Hotels At 2-Star Prices. Choose the Location, Star Rating & Amenities. Let Hotwire Find You the Best Deal. Book Today!

Hot Rate® Hotel

3.5-star Hotel in Lenox - Lee
3.5 out of 5

3.5-star Hotel

in Lenox - Lee
22 miles from Chesterfield
$65
per night
$82 total
incl. taxes & fees
3.5-star Hotel in Lenox - Lee

Hot Rate® Hotel

3-star Hotel in Lenox - Lee
3 out of 5

3-star Hotel

in Lenox - Lee
22 miles from Chesterfield
$81
per night
$101 total
incl. taxes & fees
3-star Hotel in Lenox - Lee

Hot Rate® Hotel

3-star Hotel in Pittsfield
3 out of 5

3-star Hotel

in Pittsfield
21 miles from Chesterfield
$92
per night
$114 total
incl. taxes & fees
3-star Hotel in Pittsfield

Hot Rate® Hotel

3.5-star Hotel in Northampton - Amherst - Hadley
3.5 out of 5

3.5-star Hotel

in Northampton - Amherst - Hadley
14 miles from Chesterfield
$109
per night
$140 total
incl. taxes & fees
3.5-star Hotel in Northampton - Amherst - Hadley
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Choose from 416 Chesterfield Hotel Deals

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
The price is $88 per night from May 20 to May 21
$88
per night
May 20 - May 21
Stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
7.2/10 Good! (1,005 reviews)
"The staff was great"

Reviewed on Apr 27, 2024

Quality Inn West Springfield
Howard Johnson by Wyndham Amherst Hadley
Howard Johnson by Wyndham Amherst Hadley
2 out of 5
401 Russell St, Hadley, MA
  • 6 min drive from Chesterfield Gorge
The price is $110 per night from May 5 to May 6
$110
per night
May 5 - May 6
Stay at this hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
7.2/10 Good! (1,005 reviews)
"Convenient to get around. Nice people. Room need to be updated."

Reviewed on Apr 28, 2024

Howard Johnson by Wyndham Amherst Hadley
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
  • 20 min drive from Chesterfield Gorge
The price is $160 per night from May 5 to May 6
$160
per night
May 5 - May 6
Stay at this 3-star spa hotel in Holyoke. Enjoy free breakfast, free parking, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,251 reviews)
"Missing washcloth Condition looks tired"

Reviewed on Apr 30, 2024

D. Hotel Suites & Spa
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
The price is $94 per night from May 6 to May 7
$94
per night
May 6 - May 7
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 ...
7/10 Good! (1,000 reviews)
"Clean and easy check in"

Reviewed on Apr 27, 2024

Red Roof Inn PLUS+ West Springfield
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
400 Russell St, Hadley, MA
  • 6 min drive from Chesterfield Gorge
The price is $149 per night from May 27 to May 28
$149
per night
May 27 - May 28
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 in our ...
9/10 Wonderful! (1,000 reviews)
"Awesome place to stay"

Reviewed on Apr 23, 2024

Comfort Inn & Suites
Homewood Suites by Hilton Holyoke-Springfield/North
Homewood Suites by Hilton Holyoke-Springfield/North
3 out of 5
375 Whitney Ave, Holyoke, MA
  • 38 min drive from Chesterfield Gorge
The price is $140 per night from May 29 to May 30
$140
per night
May 29 - May 30
Stay at this 3-star business-friendly hotel in Holyoke. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (836 reviews)
"Everything was great, except that when i called at 2:50 to see if room was ready they said half hour more and when i got there at 3:30 room was not ready so i had to wait til 4:30. Other than that still my favorite hotel to stay with my grandkids"

Reviewed on Apr 28, 2024

Homewood Suites by Hilton Holyoke-Springfield/North
Hotel UMass
Hotel UMass
2.5 out of 5
1 Campus Center Way, Amherst, MA
  • 10 min walk from Chesterfield Gorge
The price is $189 per night from May 1 to May 2
$189
per night
May 1 - May 2
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and room service. Popular attractions Mullins Center and UMass Fine Arts Center are located nearby. ...
8.6/10 Excellent! (736 reviews)
"Very hard to find the garage and entrance. Otherwise fine"

Reviewed on Apr 27, 2024

Hotel UMass
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
The price is $101 per night from May 27 to May 28
$101
per night
May 27 - May 28
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! (1,000 reviews)
Clean, Easy and Friendly
"We stayed one night while my daughter had a dance competition in nearby Springfield- it was about 15 minutes from the venue- Impeccably clean, great location close to the highway lots of stores and food options, breakfast was great. The staff was friendly and efficient. The hotel was very busy on ..."

Reviewed on Apr 28, 2024

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
The price is $149 per night from May 1 to May 2
$149
per night
May 1 - May 2
Stay at this 3.5-star business-friendly B&B in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (357 reviews)
Breakfast of my dreams
"Best hotel continental breakfast ever, anywhere. Comfortable and clean and friendly. Didn't care for the view of the parking lot."

Reviewed on Apr 28, 2024

The Ellery
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
The price is $179 per night from May 1 to May 2
$179
per night
May 1 - May 2
Stay at this 3-star business-friendly hotel in Hadley. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (556 reviews)
"It is a well maintained site and very convenient."

Reviewed on Apr 22, 2024

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
The price is $110 per night from May 1 to May 2
$110
per night
May 1 - May 2
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
7.4/10 Good! (1,002 reviews)
"I was in a handicapped room so the shower and bathroom were kinda weird"

Reviewed on Apr 25, 2024

Red Roof Inn PLUS+ South Deerfield – Amherst
Quality Inn
Quality Inn
2.5 out of 5
170 Housatonic Street, Lee, MA
  • 16 min drive from Chesterfield Gorge
The price is $89 per night from May 1 to May 2
$89
per night
May 1 - May 2
Stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and onsite parking. Our guests praise the breakfast and the helpful staff in our ...
8/10 Very Good! (879 reviews)
"Easy to check in and check out. The only small issue I had was that it was windy and the doors for the garbage outside kept swinging and make a bang noise when it opened and shut at night."

Reviewed on Apr 27, 2024

Quality Inn
See all 416 properties in Chesterfield
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

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 416 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 $65. 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 up to 60% 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 save up to 60% off 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 $65.

How many hotels are there in Chesterfield?

With over 416 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 $65.

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 even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Chesterfield now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chesterfield right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.