Book Hotels in Chesterfield, MA

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Top Chesterfield hotels

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
Fully refundable
$111 nightly
The price is $128 total per night from Dec 30 to Dec 31
$128 total
Dec 30 - Dec 31
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. There's ...
Well maintained hotel with a friendly staff. I was very surprised how clean and quiet the hotel was. Book this place! I’ll definitely stay here again when in the area.

Reviewed on Dec 9, 2025

Opens in a new windowBlue – A Modern Hotel, an Ascend Collection Hotel
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $135 total per night from Dec 11 to Dec 12
$135 total
Dec 11 - Dec 12
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry ...
The check in staff was excellent. Extremely polite and welcoming. Excellent hotel with a very good restaurant attached.

Reviewed on Dec 6, 2025

Opens in a new windowD. Hotel Suites & Spa
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
400 Russell St Hadley MA
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $138 total per night from Dec 28 to Dec 29
$138 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
Everything was good. Including the free breakfast

Reviewed on Dec 7, 2025

Opens in a new windowComfort Inn & Suites
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Jan 8 to Jan 9
$120 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, ...
I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the ...

Reviewed on Dec 4, 2025

Opens in a new windowBerkshire Mountain Lodge
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $135 total per night from Dec 14 to Dec 15
$135 total
Dec 14 - Dec 15
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax ...
Accommodating.

Reviewed on Dec 6, 2025

Opens in a new windowCourtyard by Marriott West Springfield
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $184 total per night from Dec 11 to Dec 12
$184 total
Dec 11 - Dec 12
Total with taxes and fees
This historic hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour ...
We liked everything!

Reviewed on Nov 29, 2025

Opens in a new windowHotel Northampton
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $99 total per night from Dec 22 to Dec 23
$99 total
Dec 22 - Dec 23
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy free perks like on-the-go breakfast and free self parking. ...
The hotel was spotless and thr beds were very comfortable

Reviewed on Dec 9, 2025

Opens in a new windowTru 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
Fully refundable
$88 nightly
The price is $99 total per night from Dec 12 to Dec 13
$99 total
Dec 12 - Dec 13
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly.

Reviewed on Dec 4, 2025

Opens in a new windowHoliday 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
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $89 total per night from Jan 4 to Jan 5
$89 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
Room was clean and smelled fine.

Reviewed on Nov 30, 2025

Opens in a new windowQuality Inn West Springfield
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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.

Chesterfield Hotel & Travel Guide\n

Do you want to have an adventure in Chesterfield? We suggest you secure accommodations as soon as you know your itinerary, as there's only 1 option within an easy driving distance of the main center of Chesterfield.

The Inn Nature Bed & Breakfast is the nearest room to the heart of Chesterfield and it is merely a brief drive away.

The Hotel Northampton is about 12 miles (20 kilometers) away from central Chesterfield. Another place to stay is the Naomi's Inn Bed & Breakfast, which is approximately 20 miles (36 kilometers) away. The Residence Inn by Marriott West Springfield and also the Hampton Inn & Suites Greenfield are two more Travelocity-listed accommodation options worth looking into around Chesterfield.

Making plans to get a little out of the center? Western Massachusetts offers many attractions. Admire the terrain of Western Massachusetts's mountains. In addition, you should explore a selection of the area's history museums. Enlightened travelers in this pocket of United States of America love skiing.

The nearest accommodation options in Franklin County include Deerfield and Bernardston. Deerfield is 17 miles (27 kilometers) to the northeast of Chesterfield, while Bernardston is 25 miles (42 kilometers) to the northeast. Travelocity-registered room options in Deerfield include the Days Inn Greenfield and Rodeway Inn. The The Log Cabin Bed & Breakfast and The Inn At Crumpin Fox are amongst the Travelocity-registered hotels and apartments in Bernardston.

Get yourself a sports fix by making the trek to Times Union Center, which you will find 50 miles (79 kilometers) to the west of Chesterfield. Those that need to find Travelocity-listed accommodation options in the area surrounding the stadium can select from the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

When you're flying via Bradley International Airport and choose to base yourself nearby, try Sheraton Hartford Hotel at Bradley Airport or Holiday Inn Express & Suites Bradley Airport.

Frequently asked questions

What are the top kid-friendly hotels in Chesterfield?
Take some of the hassles out of traveling with kids by staying in a family-friendly hotel in Chesterfield. From entertaining amenities to services that bring a smile, these properties offer perks that'll make your getaway smooth sailing: Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck! will help make your vacation the best one yet. It comes with a range of conveniences geared toward families, such as a deck and a fireplace. Elegant Wilderness Cabin 12 Miles From Northampton is another great choice. After a fun day of exploring, come back home to your comfortable room and amenities like a water park and animal viewing activities.
Where can I find cheap hotels in Chesterfield?
At Travelocity you'll find really nice hotels in Chesterfield at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chesterfield rather than in Chesterfield. We may find you even better rates, too.
How do I find the best Chesterfield hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chesterfield then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chesterfield?
The cheapest hotel in Chesterfield is $89. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chesterfield?
There are 484 hotels in Chesterfield on Travelocity.
What are the best hotels in Chesterfield?
Chesterfield has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chesterfield for you!
When is the best time to visit Chesterfield?
If you want the joy of a fun-filled trip in peak season, visit Chesterfield during June, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Chesterfield?
Based on historic data is usually the cheapest month to visit Chesterfield. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chesterfield?
There are multiple hotels in Chesterfield that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chesterfield. We have plenty of kid-friendly hotels in Chesterfield to choose from on Travelocity!
Why book a hotel in Chesterfield through Travelocity?
Because we have the top hotels in Chesterfield! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chesterfield on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chesterfield hotel reviews by fellow wanderers

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"The hotel was spotless and thr beds were very comfortable "
A verified traveler stayed at Tru by Hilton Chicopee Springfield
Tru by Hilton Chicopee Springfield

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