Find hotels in Chesterfield, MA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Filter by

Guest rating
Guest rating
Star rating

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

Balcony
Inn on Boltwood

Inn on Boltwood

3.0 star property
Amherst
9.4 out of 10, Exceptional, (741)
"Such a treat to stay here!"
United States
Elizabeth
Inn on Boltwood
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (962)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 328
AED 366 total
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AED 364
AED 407 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very Good, (785)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is AED 291
AED 333 total
includes taxes & fees
12 Dec - 13 Dec
Candlewood Suites West Springfield by IHG
Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (798)
"Clean room and staff was super friendly"
United States
Yuen
The price is AED 490
AED 547 total
includes taxes & fees
22 Dec - 23 Dec
Hotel On North
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (97)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is AED 400
AED 447 total
includes taxes & fees
23 Nov - 24 Nov
River Valley Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (763)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Lobby
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 star property
West Springfield
6.8 out of 10, (1004)
"Great like always "
United States
Sharee
The price is AED 304
AED 348 total
includes taxes & fees
1 Dec - 2 Dec
Red Roof Inn PLUS+ West Springfield
Check-in/check-out kiosk
Quality Inn West Springfield

Quality Inn West Springfield

2.5 star property
West Springfield
7.0 out of 10, Good, (1015)
"Room and staff were good "
United States
George
The price is AED 330
AED 378 total
includes taxes & fees
30 Nov - 1 Dec
Quality Inn West Springfield
Property amenity
Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

3.0 star property
Hadley
9.0 out of 10, Wonderful, (678)
"Nice and quiet and conveniently located very close to UMass"
United States
Connor
The price is AED 525
AED 587 total
includes taxes & fees
30 Nov - 1 Dec
Courtyard by Marriott Hadley Amherst
Lobby
Hotel UMass

Hotel UMass

2.5 star property
Amherst
8.8 out of 10, Excellent, (1004)
"Great on campus location!"
United States
Shuhui
The price is AED 409
AED 461 total
includes taxes & fees
14 Dec - 15 Dec
Hotel UMass
Lobby
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
Northampton
9.2 out of 10, Wonderful, (1003)
"Clean room great breakfast selections would stay here again"
United States
Mary
The price is AED 525
AED 587 total
includes taxes & fees
30 Nov - 1 Dec
Fairfield Inn & Suites Springfield Northampton/Amherst
View from property
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3.0 star property
West Springfield
9.2 out of 10, Wonderful, (567)
"Room was clean and staff was super friendly "
United States
Jessuca
The price is AED 434
AED 497 total
includes taxes & fees
30 Nov - 1 Dec
Courtyard by Marriott West Springfield
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1002)
"Clean room and good breakfast "
United States
Kelly
The price is AED 340
AED 380 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 star property
West Springfield
9.6 out of 10, Exceptional, (92)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is AED 399
AED 456 total
includes taxes & fees
14 Dec - 15 Dec
Blue – A Modern Hotel, an Ascend Collection Hotel
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2256)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is AED 314
AED 365 total
includes taxes & fees
30 Nov - 1 Dec
D. Hotel Suites & Spa
Lobby
Comfort Inn & Suites

Comfort Inn & Suites

2.5 star property
Hadley
9.2 out of 10, Wonderful, (1012)
"Hotel was clean, bed was comfortable, staff was friendly and good breakfast options. "
United States
Brandi
The price is AED 465
AED 520 total
includes taxes & fees
30 Nov - 1 Dec
Comfort Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (810)
"Room spotless and staff helpful."
United States
William
The price is AED 275
AED 308 total
includes taxes & fees
23 Nov - 24 Nov
FairBridge Inn Express
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (345)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AED 328
AED 366 total
includes taxes & fees
23 Nov - 24 Nov
The Central Downtown Inn & Suites
Indoor pool
Comfort Inn & Suites West Springfield

Comfort Inn & Suites West Springfield

2.5 star property
West Springfield
7.6 out of 10, Good, (896)
"Great location, clean staff was very very friendly"
United States
Kerry
The price is AED 409
AED 468 total
includes taxes & fees
17 Dec - 18 Dec
Comfort Inn & Suites West Springfield
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Chesterfield attractions

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.
See properties

Chesterfield Public Library

Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
See properties

Top Chesterfield Hotel Reviews

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Room was amazing... comfortable setting. Wonderful Staff!! I will definitely be back for future stays."
Eddilio 1-night trip
Posted 14 hours ago
Tru by Hilton Chicopee Springfield

Hotels in Chesterfield with star-rating

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 Holiday Inn & Suites Pittsfield-Berkshires by IHG. 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 483 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 Chesterfield Gorge, Westfield River, 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.

Explore a world of travel with Expedia