Book Hotels in Chesterfield, MA

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

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
$110 nightly
The price is $125 total per night from Aug 23 to Aug 24
$125 total
Aug 23 - Aug 24
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 ...
"Clean, friendly staff"

Reviewed on Jul 28, 2026

Opens in a new windowBlue – A Modern Hotel, an Ascend Collection Hotel
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
$145 nightly
The price is $162 total per night from Aug 2 to Aug 3
$162 total
Aug 2 - Aug 3
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. Enjoy ...
"Nice stay at this Holiday Express in Pittsfield. The staff were so polite and helpful, building looked brand new. My husband and I were happy with the gym equipment, the pool looked nice and clean as well. Excellent complimentary breakfast that went until 10:00. 😊 Definitely recommend!!!!"

Reviewed on Jul 24, 2026

Opens in a new windowHoliday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street West Springfield MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $115 total per night from Aug 9 to Aug 10
$115 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock ...
"Had people outside my door until 3:30am being loud not caring."

Reviewed on Jul 27, 2026

Opens in a new windowRed Roof Inn PLUS+ West Springfield
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundable
$95 nightly
The price is $108 total per night from Aug 11 to Aug 12
$108 total
Aug 11 - Aug 12
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 ...
"A lot of dining options around"

Reviewed on Jul 28, 2026

Opens in a new windowQuality Inn West Springfield
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundable
$142 nightly
The price is $158 total per night from Aug 9 to Aug 10
$158 total
Aug 9 - Aug 10
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 ...
Opens in a new windowD. Hotel Suites & Spa
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$142 nightly
The price is $158 total per night from Aug 27 to Aug 28
$158 total
Aug 27 - Aug 28
Total with taxes and fees
This aparthotel 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 ...
Opens in a new windowBerkshire Mountain Lodge
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 Aug 4 to Aug 5
$184 total
Aug 4 - Aug 5
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 ...
Opens in a new windowHotel Northampton
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 out of 5
1011 Riverdale St West Springfield MA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $121 total per night from Aug 9 to Aug 10
$121 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
Opens in a new windowHampton Inn West Springfield
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
Fully refundable
$144 nightly
The price is $161 total per night from Aug 9 to Aug 10
$161 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features 5 coffee shops/cafes and a bar/lounge. Enjoy a meal from the restaurant and perks like free continental breakfast and free WiFi. Self parking, ...
Opens in a new windowHotel UMass
Don't see what you're looking for?
See all available properties in Chesterfield
View all properties
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 $108. 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 507 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

Quality Inn West Springfield

Quality Inn West Springfield

4 out of 5
Posted 8 hours ago
Travelocity Verified Review
"A lot of dining options around"
A verified traveler stayed at Quality Inn West Springfield
Quality Inn West Springfield

Explore More Ways to Travel with Travelocity