Book Hotels in Chesterfield, MA

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Top Chesterfield hotels

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
$124 nightly
The price is $139 total per night from Jan 26 to Jan 27
$139 total
Jan 26 - Jan 27
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 ...
Great, great place!

Reviewed on Jan 22, 2026

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
$110 nightly
The price is $122 total per night from Feb 15 to Feb 16
$122 total
Feb 15 - Feb 16
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 clean and very nice.

Reviewed on Jan 8, 2026

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
$121 nightly
The price is $136 total per night from Feb 22 to Feb 23
$136 total
Feb 22 - Feb 23
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, ...
Clean, great location near Bosquet Mountain and grocery store, spacious condo, easy.

Reviewed on Jan 19, 2026

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 Jan 29 to Jan 30
$135 total
Jan 29 - Jan 30
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 ...
Clean, great area, and welcoming.

Reviewed on Jan 8, 2026

Opens in a new windowCourtyard by Marriott West Springfield
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Jan 27 to Jan 28
$133 total
Jan 27 - Jan 28
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden, a lobby fireplace, and a picnic ...
Each visit, I've found the rooms, bed and bath clean and comfortable. The breakfast options are very thoughtful and help me start the day well. The staff at check in and check out are kind and attentive. It is nice to enjoy time by a fireplace, and the occasional puzzle at a table is a fun ...

Reviewed on Jan 19, 2026

Opens in a new windowThe Ellery
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
$165 nightly
The price is $184 total per night from Jan 25 to Jan 26
$184 total
Jan 25 - Jan 26
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 ...
Perfect hotel choice for attending an event at Iron Horse ~ clean room, lovely staff and great central location

Reviewed on Jan 17, 2026

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
$89 nightly
The price is $101 total per night from Feb 1 to Feb 2
$101 total
Feb 1 - Feb 2
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. ...
Johnathan at the front desk is a prime example of exemplary customer service. I was blown away by his willingness to help all guests not just myself.

Reviewed on Jan 19, 2026

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
$98 nightly
The price is $109 total per night from Jan 30 to Jan 31
$109 total
Jan 30 - Jan 31
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 ...
generally good

Reviewed on Jan 19, 2026

Opens in a new windowHoliday 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
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $102 total per night from Jan 28 to Jan 29
$102 total
Jan 28 - Jan 29
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are ...
Execellent

Reviewed on Jan 16, 2026

Opens in a new windowRed Roof Inn PLUS+ South Deerfield – Amherst
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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 $101. 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 502 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

D. Hotel Suites & Spa

D. Hotel Suites & Spa

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Great, great place!"
A verified traveler stayed at D. Hotel Suites & Spa
D. Hotel Suites & Spa

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