Find hotels in Chesterfield, MA from ฿2,441

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
29 Oct - 30 Oct
Tomorrow
30 Oct - 31 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Filter by

Guest rating
Guest rating
Star rating

Top 10 Chesterfield hotels and places to stay

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (930)
"Friendly staff and clean rooms. Loved the onsite restaurant & bar."
United States
Carmen
The price is ฿3,335
฿3,725 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Balcony
Inn on Boltwood
Inn on Boltwood
3.0 star property
9.4 out of 10, Exceptional, (735)
"Really enjoyed the stay, great atmosphere and excellent service."
Canada
Mark
Inn on Boltwood
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is ฿4,100
฿4,580 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn
River Valley Inn
2.0 star property
8.6 out of 10, Excellent, (86)
"Great quiet motel. "
United States
Hector
The price is ฿3,853
฿4,303 total
includes taxes & fees
9 Nov - 10 Nov
River Valley Inn
Exterior
Candlewood Suites West Springfield by IHG
Candlewood Suites West Springfield by IHG
2.5 star property
8.4 out of 10, Very good, (776)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is ฿3,173
฿3,631 total
includes taxes & fees
12 Nov - 13 Nov
Candlewood Suites West Springfield by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (739)
"Great stay, perfect "
United States
Lawrence
Berkshire Mountain Lodge
Lobby
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 star property
6.8 out of 10, (1001)
"The staff was very helpful and nice"
United States
Cristal
The price is ฿3,176
฿3,634 total
includes taxes & fees
5 Nov - 6 Nov
Red Roof Inn PLUS+ West Springfield
Front of property – evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (786)
"Clean room, great location. Restaurant phenomenal "
United States
Mary
The price is ฿3,626
฿4,050 total
includes taxes & fees
3 Nov - 4 Nov
Hotel On North
Lobby
Hotel UMass
Hotel UMass
2.5 star property
8.8 out of 10, Excellent, (1004)
"Great stay!"
United States
Julie
The price is ฿4,578
฿5,150 total
includes taxes & fees
9 Nov - 10 Nov
Hotel UMass
Check-in/check-out kiosk
Quality Inn West Springfield
Quality Inn West Springfield
2.5 star property
7.0 out of 10, Good, (1036)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
United States
Danielle
The price is ฿2,614
฿2,992 total
includes taxes & fees
16 Nov - 17 Nov
Quality Inn West Springfield
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
5.4 out of 10, (799)
"Good service and people"
United States
Jerod
The price is ฿2,185
฿2,441 total
includes taxes & fees
12 Nov - 13 Nov
FairBridge Inn Express
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel
Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
9.4 out of 10, Exceptional, (68)
"Wonderful staff and beautiful new, clean rooms!"
United States
Lori
The price is ฿4,100
฿4,693 total
includes taxes & fees
23 Nov - 24 Nov
Blue – A Modern Hotel, an Ascend Collection Hotel
Lobby
Fairfield Inn & Suites Springfield Northampton/Amherst
Fairfield Inn & Suites Springfield Northampton/Amherst
3.0 star property
9.2 out of 10, Wonderful, (1003)
"Clean room and friendly staff."
United States
Mark
The price is ฿4,921
฿5,497 total
includes taxes & fees
16 Nov - 17 Nov
Fairfield Inn & Suites Springfield Northampton/Amherst
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (333)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
The price is ฿3,137
฿3,504 total
includes taxes & fees
2 Nov - 3 Nov
The Central Downtown Inn & Suites
Lobby
Quality Inn
Quality Inn
2.5 star property
8.4 out of 10, Very good, (1004)
"Staff was very helpful - easy location - clean rooms!"
United States
Karen
The price is ฿2,999
฿3,350 total
includes taxes & fees
16 Nov - 17 Nov
Quality Inn
Indoor pool
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3.0 star property
9.4 out of 10, Exceptional, (2270)
"Very comfortable rooms. Excellent restaurant on site. "
United States
Lynette
The price is ฿3,558
฿4,133 total
includes taxes & fees
3 Nov - 4 Nov
D. Hotel Suites & Spa
View from property
Courtyard by Marriott West Springfield
Courtyard by Marriott West Springfield
3.0 star property
9.2 out of 10, Wonderful, (553)
"Room was clean and staff was super friendly "
United States
Jessuca
The price is ฿3,825
฿4,378 total
includes taxes & fees
13 Nov - 14 Nov
Courtyard by Marriott West Springfield
Property amenity
Courtyard by Marriott Hadley Amherst
Courtyard by Marriott Hadley Amherst
3.0 star property
9.0 out of 10, Wonderful, (672)
"Great stay"
United States
Alan
The price is ฿5,212
฿5,822 total
includes taxes & fees
16 Nov - 17 Nov
Courtyard by Marriott Hadley Amherst
Lobby
Comfort Inn & Suites
Comfort Inn & Suites
2.5 star property
9.2 out of 10, Wonderful, (1027)
"Hotel was clean, bed was comfortable, staff was friendly and good breakfast options. "
United States
Brandi
The price is ฿4,100
฿4,580 total
includes taxes & fees
16 Nov - 17 Nov
Comfort Inn & Suites
Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
7.2 out of 10, Good, (1047)
"Great location"
United States
Linda
The price is ฿2,768
฿3,092 total
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn PLUS+ South Deerfield – Amherst
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
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 forests while you're in the area.
See properties

Krug Sugarbush

You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops.
See properties

Top Chesterfield Hotel Reviews

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"Clean and modern. Fancy. "
Andrew 1-night trip
Posted 2 days ago
Blue – A Modern Hotel, an Ascend Collection Hotel

More cheap stays in Chesterfield

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street, West Springfield, MA
The price is ฿3,176 per night from 5 Nov to 6 Nov
฿3,176
฿3,634 total
5 Nov - 6 Nov
includes taxes & fees
6.8/10 (1,004 reviews)

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 traveller data. Two other choices for your visit to the area are Quality Inn West Springfield and D. Hotel Suites & Spa. See all available top hotels, or vacation rentals in Chesterfield.
If I need to cancel my hotel reservation in Chesterfield, will I receive a refund?
Yes, you'll find most hotel room reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chesterfield.
What is staying in Chesterfield like?
Visitors can enjoy all that Chesterfield has to offer, including the restaurants, shopping and parks. There are 481 hotels and other accommodation options in the surrounding area. Find out more about Chesterfield.
What should I do while I'm visiting Chesterfield?
Natural beauty is on display at Chesterfield Gorge, Westfield River and Knightville Dam & Reservation. A couple of additional sights to add to your itinerary are Chesterfield Public Library and Chesterfield Town Hall. Take a look at what more there is to see and do in Expedia's Chesterfield guide.
What's the seasonal weather in Chesterfield?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chesterfield are January, February, November and March, with each month seeing an average of 16 cm of snowfall.

Explore a world of travel with Expedia