Book Cheap Hotels in Chesterfield

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Check prices in Chesterfield for tonight, Dec 21 - Dec 22
Dec 21 - Dec 22
Tomorrow night
Check prices in Chesterfield for tomorrow night, Dec 22 - Dec 23
Dec 22 - Dec 23
Next weekend
Check prices in Chesterfield for next weekend, Dec 26 - Dec 28
Dec 26 - Dec 28

Most frequently booked Chesterfield hotels

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free cancellation
Reserve now, pay when you stay
23.29 km from city centre
The price is CA $151 per night
CA $151
CA $175 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Mount Tom State Reservation and Nash's Dinosaur Track Quarry are located nearby.
Pool
Hot tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
34.67 km from city centre
The price is CA $128 per night
CA $128
CA $143 total
Dec 23 - Dec 24
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
34.87 km from city centre
The price is CA $136 per night
CA $136
CA $183 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
Pool
Hot tub
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free cancellation
Reserve now, pay when you stay
33.46 km from city centre
The price is CA $109 per night
CA $109
CA $124 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions MGM Springfield and Olympia Ice Center are located nearby.
Pool
Breakfast included
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
Free cancellation
Reserve now, pay when you stay
34.25 km from city centre
The price is CA $163 per night
CA $163
CA $187 total
Dec 24 - Dec 25
includes taxes & fees
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MGM Springfield and Six Flags New England are located nearby.
Pool
Parking included
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
400 Russell St Hadley MA
Free cancellation
Reserve now, pay when you stay
24.38 km from city centre
The price is CA $171 per night
CA $171
CA $191 total
Dec 28 - Dec 29
includes taxes & fees
Book a 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 reviews. Popular attractions Autobahn and Cinemark At Hampshire Mall are located nearby.
Pool
Breakfast included
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
Free cancellation
33.62 km from city centre
The price is CA $160 per night
CA $160
CA $184 total
Jan 18 - Jan 19, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions MGM Springfield and Riverdale Shops are located nearby.
Parking included
Free WiFi
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
Free cancellation
Reserve now, pay when you stay
32.74 km from city centre
The price is CA $123 per night
CA $123
CA $140 total
Dec 30 - Dec 31
includes taxes & fees
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 attractions MGM Springfield and Chicopee Falls Dam are located nearby.
Pool
Breakfast included
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
18.94 km from city centre
Get rates
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Calvin Theater and Calvin Theatre and Performing Arts Center are located nearby.
Parking included
Free WiFi
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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 hotels essential information

Accommodation
487 hotels
Lowest Price
CA $124
Highest Price
CA $191
Popular hotels
D. Hotel Suites & Spa, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshire Mountain Lodge, Quality Inn West Springfield, Courtyard by Marriott West Springfield, Comfort Inn & Suites, Blue – A Modern Hotel, an Ascend Collection Hotel, Tru by Hilton Chicopee Springfield, Hotel Northampton

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 CA $124 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 487 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

Hotel Northampton

Hotel Northampton

5 out of 5
Posted 7 hours ago
Travelocity Verified Review
"Great, gracious hotel with old time charm. Clean and comfortable too."
A verified traveller stayed at Hotel Northampton
Hotel Northampton

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