Find hotels in Chesterfield, MA from CA $107

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Compare 466 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Chesterfield hotels

Inn on Boltwood

3.0 star property
9.4 out of 10, Exceptional, (702)
"this is a gem of a hotel right in the center of town , great food ,friendly staff ."
The price is CA $287
CA $320 total
includes taxes & fees
Sep 2 - Sep 3
Inn on Boltwood

River Valley Inn

2.0 star property
8.6 out of 10, Excellent, (40)
"Great quiet motel. "
The price is CA $179
CA $200 total
includes taxes & fees
Aug 24 - Aug 25
River Valley Inn

Quality Inn West Springfield

2.5 star property
7.0 out of 10, Good, (1000)
"My daughter and the kids said it was perfect for their overnight stay after visiting Six Flags. "
The price is CA $123
CA $140 total
includes taxes & fees
Sep 7 - Sep 8
Quality Inn West Springfield

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (20)
"Really enjoyed my stay here, definitely need a car to get around"
The price is CA $188
CA $210 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is CA $99
CA $110 total
includes taxes & fees
Aug 24 - Aug 25
FairBridge Inn Express

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1000)
"Rooms were clean and the staff was nice. "
The price is CA $124
CA $142 total
includes taxes & fees
Aug 31 - Sep 1
Red Roof Inn PLUS+ West Springfield

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (863)
"Consistently a clean room with welcoming staff."
The price is CA $152
CA $169 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (584)
"Amazing place to stay. Can’t wait to go again. "
The price is CA $107
CA $150 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (744)
"I would definitely stay here again!"
The price is CA $143
CA $164 total
includes taxes & fees
Sep 1 - Sep 2
Candlewood Suites West Springfield by IHG

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (758)
"Quite and good location to around towns"
The price is CA $244
CA $273 total
includes taxes & fees
Aug 24 - Aug 25
Hotel On North

Hotel UMass

2.5 star property
8.8 out of 10, Excellent, (1002)
"Enjoyed our stay"
The price is CA $219
CA $246 total
includes taxes & fees
Sep 3 - Sep 4
Hotel UMass

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
9.2 out of 10, Wonderful, (977)
"The place is amazing "
The price is CA $211
CA $236 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites Springfield Northampton/Amherst

Courtyard by Marriott West Springfield

3.0 star property
9.2 out of 10, Wonderful, (496)
"Friendly staff and very clean. "
The price is CA $195
CA $223 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott West Springfield

Courtyard by Marriott Hadley Amherst

3.0 star property
9.0 out of 10, Wonderful, (645)
"Good location..well maintained..friendly staff."
The price is CA $249
CA $278 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Hadley Amherst

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is CA $152
CA $170 total
includes taxes & fees
Sep 8 - Sep 9
Quality Inn

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2229)
"I enjoyed my stay "
The price is CA $144
CA $167 total
includes taxes & fees
Aug 24 - Aug 25
D. Hotel Suites & Spa

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Great place to stay"
The price is CA $200
CA $223 total
includes taxes & fees
Sep 3 - Sep 4
Comfort Inn & Suites

Pilgrim Inn

2.5 star property
5.8 out of 10, (314)
"Great location but no staff at check-in or checkout!"
The price is CA $111
CA $124 total
includes taxes & fees
Aug 24 - Aug 25
Pilgrim Inn

Best Western Springfield West Inn

2.5 star property
7.8 out of 10, Good, (1003)
"Great stay"
The price is CA $130
CA $149 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Springfield West Inn

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (307)
"Clean and convenient."
The price is CA $152
CA $169 total
includes taxes & fees
Sep 14 - Sep 15
The Central Downtown Inn & Suites
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.
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Learn more about Chesterfield

Get away to Chesterfield! Enjoy the adventure, local cuisine, and natural setting.

Stay near popular Chesterfield attractions

Chesterfield Gorge

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area.

Frequently asked questions

Where is the best place to stay in Chesterfield?

Located 21.7 mi (34.9 km) from the heart of Chesterfield, Berkshire Mountain Lodge is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Quality Inn West Springfield and D. Hotel Suites & Spa. See all available top hotels, or vacation rentals in Chesterfield.

What are some of the best vacation rentals that Chesterfield has to offer?

Peace and quiet on the lake: Visitors like this Chesterfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. See all vacation rentals in Chesterfield.

If I need to cancel my hotel reservation in Chesterfield, will I receive a refund?

Yes, most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chesterfield.

Where can I learn more about changing or cancelling my trip to Chesterfield?

For additional details about rescheduling or cancelling your trip to Chesterfield, click here.

Where is the best place to stay close to Chesterfield Gorge?

Fiddlehead Inn is one of the top choices for your stay based on our traveler data, and this 3-star inn offers a restaurant and free parking. It's located 2.9 mi (4.7 km) from Chesterfield Gorge. Another good choice is Charming Farmhouse - quiet, private & peaceful , located 3 mi (4.9 km) away.

What's the best hotel for staying near Logan International Airport (BOS)?

Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.

What is staying in Chesterfield like?

Visitors can enjoy all that Chesterfield has to offer including the restaurants, shopping, and parks. There are 467 hotels and other accommodations in the surrounding area. Find out more about Chesterfield.

What should I see while I'm in Chesterfield?

Natural beauty is on display at Westfield River, Chesterfield Gorge, and Knightville Dam & Reservation. A couple of additional sights to add to your agenda are Chesterfield Public Library and Chesterfield Town Hall. Check out what more to see and do in Expedia's Chesterfield guide.

What's the weather like in Chesterfield?

The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.