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
The price is $132 total per night from Apr 7 to Apr 8
$132 total
per night
Apr 7 - Apr 8
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 ...
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

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
The price is $135 total per night from Mar 10 to Mar 11
$135 total
per night
Mar 10 - Mar 11
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 amenities. Nice room. Great staff

Reviewed on Mar 9, 2026

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

Comfort Inn & Suites Hadley - Amherst

2.5 out of 5
400 Russell St Hadley MA
Fully refundableReserve now, pay when you stay
The price is $121 total per night from Mar 22 to Mar 23
$121 total
per night
Mar 22 - Mar 23
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 ...
Beautiful view from rooftop pool

Reviewed on Mar 8, 2026

Opens in a new windowComfort Inn & Suites Hadley - Amherst
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
The price is $145 total per night from Mar 15 to Mar 16
$145 total
per night
Mar 15 - Mar 16
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 ...
Stayed here because I was having the floors in my house redone everything was clean crispy everything worked no problems with that but I don’t know if there was a generator or the heating air ducts that were allowed enough that I left the TV on at night and the TV must collect some kind of satellite ...

Reviewed on Mar 2, 2026

Opens in a new windowCourtyard by Marriott West Springfield
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

3 out of 5
115A Conz Street Northampton MA
Fully refundableReserve now, pay when you stay
The price is $170 total per night from Mar 17 to Mar 18
$170 total
per night
Mar 17 - Mar 18
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with ...
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

Opens in a new windowFairfield Inn & Suites Springfield Northampton/Amherst
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
Fully refundableReserve now, pay when you stay
The price is $138 total per night from Mar 22 to Mar 23
$138 total
per night
Mar 22 - Mar 23
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 ...
Property was cute - a redone motel with a hipster style and vibe. Good breakfast offering and easy drive to Smith’s campus and downtown (but not walkable IMO). Bed was comfortable and all was clean. Main complaint was you could hear the upstairs room and people outside the door. Very little soundproofing. ...

Reviewed on Mar 8, 2026

Opens in a new windowThe Ellery
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is $128 total per night from Apr 7 to Apr 8
$128 total
per night
Apr 7 - Apr 8
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, ...
The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after ...

Reviewed on Mar 6, 2026

Opens in a new windowBerkshire Mountain Lodge
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
The price is $142 total per night from Mar 31 to Apr 1
$142 total
per night
Mar 31 - Apr 1
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 ...
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

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
The price is $95 total per night from Apr 1 to Apr 2
$95 total
per night
Apr 1 - Apr 2
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 ...
The door to my room was broken. "Just throw your weight into it," should not be the instructions from hotel staff. The handle/latch had been troublesome for a while, judging by the instructions on the handle (on this room only) to pull up on the handle, not down, to open the door. I made so much ...

Reviewed on Feb 23, 2026

Opens in a new windowRed Roof Inn PLUS+ South Deerfield – Amherst
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See all available properties in Chesterfield
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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 $95. 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 514 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

The Ellery

The Ellery

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"This is a very special place. The rooms are very well thought out with many intelligent details that made my stay more comfortable. Great breakfast. The coffee is organic :). The staff are always available and very responsive. Also it is quiet!! I love this place"
A verified traveler stayed at The Ellery
The Ellery

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