Chesterfield Hotels

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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chesterfield hotels

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (959)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is P5,209
P5,818 total
includes taxes & fees
Nov 21 - Nov 22
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very Good, (785)
"staff was great! the borrow cabinet is an awesome feature and the pool and hot tub were amazing!"
United States
Kelly
The price is P5,787
P6,624 total
includes taxes & fees
Nov 19 - Nov 20
Candlewood Suites West Springfield 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 P6,224
P6,953 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (758)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (96)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is P6,437
P7,190 total
includes taxes & fees
Nov 18 - Nov 19
River Valley Inn

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (797)
"Clean room and staff was super friendly"
United States
Yuen
The price is P7,877
P8,799 total
includes taxes & fees
Nov 20 - Nov 21
Hotel On North

Red Roof Inn PLUS+ West Springfield

2.5 star property
West Springfield
6.8 out of 10, (1002)
"Excellent "
United States
Laurence
The price is P4,890
P5,596 total
includes taxes & fees
Dec 1 - Dec 2
Red Roof Inn PLUS+ West Springfield

Quality Inn West Springfield

2.5 star property
West Springfield
7.0 out of 10, Good, (1008)
"Room and staff were good "
United States
George
The price is P4,977
P5,696 total
includes taxes & fees
Dec 7 - Dec 8
Quality Inn West Springfield

Hotel UMass

2.5 star property
Amherst
8.8 out of 10, Excellent, (1003)
"Great on campus location!"
United States
Shuhui
The price is P7,418
P8,352 total
includes taxes & fees
Nov 23 - Nov 24
Hotel UMass

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 P8,445
P9,433 total
includes taxes & fees
Nov 30 - Dec 1
Fairfield Inn & Suites Springfield Northampton/Amherst

Courtyard by Marriott Hadley Amherst

3.0 star property
Hadley
9.0 out of 10, Wonderful, (678)
"Great stay"
United States
Alan
The price is P8,445
P9,433 total
includes taxes & fees
Nov 30 - Dec 1
Courtyard by Marriott Hadley Amherst

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 P6,475
P7,411 total
includes taxes & fees
Dec 7 - Dec 8
Blue – A Modern Hotel, an Ascend Collection Hotel

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2248)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is P6,490
P7,539 total
includes taxes & fees
Nov 18 - Nov 19
D. Hotel Suites & Spa

Courtyard by Marriott West Springfield

3.0 star property
West Springfield
9.2 out of 10, Wonderful, (567)
"Work trip meet my needs"
United States
Thomas
The price is P6,977
P7,986 total
includes taxes & fees
Nov 23 - Nov 24
Courtyard by Marriott West Springfield

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (809)
"Room spotless and staff helpful."
United States
William
The price is P4,429
P4,948 total
includes taxes & fees
Nov 18 - Nov 19
FairBridge Inn Express

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (344)
"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 P5,274
P5,891 total
includes taxes & fees
Nov 18 - Nov 19
The Central Downtown Inn & Suites

Comfort Inn & Suites

2.5 star property
Hadley
9.2 out of 10, Wonderful, (1009)
"Great stay!"
United States
Erin
The price is P7,479
P8,354 total
includes taxes & fees
Nov 19 - Nov 20
Comfort Inn & Suites

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1001)
"Clean room and good breakfast "
United States
Kelly
The price is P5,471
P6,112 total
includes taxes & fees
Nov 30 - Dec 1
Quality Inn

Comfort Inn & Suites West Springfield

2.5 star property
West Springfield
7.6 out of 10, Good, (895)
"Great location, clean staff was very very friendly"
United States
Kerry
The price is P6,562
P7,510 total
includes taxes & fees
Dec 14 - Dec 15
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chesterfield attractions

Top Chesterfield Hotel Reviews

More cheap stays in Chesterfield

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.
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.
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.