Find hotels in Chesterfield, MA from ฿2,443

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7 Nov - 8 Nov
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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
Pittsfield
8.0 out of 10, Very good, (941)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is ฿3,175
฿3,546 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Balcony
Inn on Boltwood

Inn on Boltwood

3.0 star property
Amherst
9.4 out of 10, Exceptional, (736)
"Great stay"
United States
Pellegrino
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
Pittsfield
9.4 out of 10, Exceptional, (56)
"Bright new hotel with very friendly and helpful staff. "
United States
Mary
The price is ฿3,828
฿4,276 total
includes taxes & fees
2 Dec - 3 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, (780)
"staff was great! the borrow cabinet is an awesome feature and the pool and hot tub were amazing!"
United States
Kelly
The price is ฿3,175
฿3,634 total
includes taxes & fees
17 Nov - 18 Nov
Candlewood Suites West Springfield by IHG
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, (90)
"Room was very clean. Owners are great Close to all things in Deerfield Would definitely stay there again "
United States
Kenneth
The price is ฿3,855
฿4,306 total
includes taxes & fees
11 Nov - 12 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, (748)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
Berkshire Mountain Lodge
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (792)
"Perfect Stay in the Berkshire This hotel was spacious, clean, and had everything needed for a comfortable stay. The room was well-maintained, and the location was ideal—close to local attractions and easy to get around. Smooth check-in process and great access throughout. Highly recommend! "
United States
Ann
The price is ฿4,321
฿4,827 total
includes taxes & fees
16 Nov - 17 Nov
Hotel On North
Lobby
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 star property
West Springfield
6.8 out of 10, (1000)
"Excellent "
United States
Laurence
The price is ฿2,741
฿3,137 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, (1001)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
United States
Danielle
The price is ฿2,807
฿3,213 total
includes taxes & fees
4 Dec - 5 Dec
Quality Inn West Springfield
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (807)
"Room spotless and staff helpful."
United States
William
The price is ฿2,187
฿2,443 total
includes taxes & fees
23 Nov - 24 Nov
FairBridge Inn Express
Lobby
Hotel UMass

Hotel UMass

2.5 star property
Amherst
8.8 out of 10, Excellent, (1001)
"Wonderful place to stay "
United States
Chin-Wen
The price is ฿4,325
฿4,868 total
includes taxes & fees
10 Nov - 11 Nov
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, (1008)
"Staff were accommodating. The rooms were great. The location is perfect for a visit to Northampton. I’d stay again or recommend others to book a stay. "
United States
Winifred
The price is ฿4,341
฿4,849 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites Springfield Northampton/Amherst
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, (81)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is ฿3,563
฿4,078 total
includes taxes & fees
7 Dec - 8 Dec
Blue – A Modern Hotel, an Ascend Collection Hotel
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very good, (1000)
"Fine lodging for short term business stay"
United States
Lawrence
The price is ฿2,831
฿3,162 total
includes taxes & fees
1 Dec - 2 Dec
Quality Inn
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.8 out of 10, Excellent, (339)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ฿3,662
฿4,091 total
includes taxes & fees
8 Nov - 9 Nov
The Central Downtown Inn & Suites
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2280)
"Great hotel, spacious room, and pleasant staff. We enjoyed our stay and had no issues. Would definitely stay here again. "
United States
Gloria
The price is ฿3,560
฿4,136 total
includes taxes & fees
23 Nov - 24 Nov
D. Hotel Suites & Spa
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, (559)
"The hotel is wonderful and located close to shopping and some nice local restaurants. The staff was very attentive and thoughtful."
United States
Kathleen
The price is ฿3,828
฿4,381 total
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott 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, (672)
"Great stay"
United States
Alan
The price is ฿4,378
฿4,891 total
includes taxes & fees
30 Nov - 1 Dec
Courtyard by Marriott Hadley Amherst
Lobby
Comfort Inn & Suites

Comfort Inn & Suites

2.5 star property
Hadley
9.2 out of 10, Wonderful, (1001)
"Hotel was clean, bed was comfortable, staff was friendly and good breakfast options. "
United States
Brandi
The price is ฿4,076
฿4,552 total
includes taxes & fees
30 Nov - 1 Dec
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
South Deerfield
7.2 out of 10, Good, (1000)
"Parking was great. Food in the area was good. Staff was nice. "
United States
Gabriel
The price is ฿2,770
฿3,094 total
includes taxes & fees
13 Nov - 14 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.
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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

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"The area is not good looking, but the hotel is pretty good, it is clean, super friendly staff, eco friendly, everything looks new, decent breakfast, I love it and I recommend you this place"
GLAYJOS 1-night trip
Posted 4 days ago
Tru by Hilton Chicopee Springfield
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

10/10 Excellent
"Excellent "
Laurence 1-night trip
Posted 3 weeks ago
Red Roof Inn PLUS+ West Springfield

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 ฿2,741 per night from 1 Dec to 2 Dec
฿2,741
฿3,137 total
1 Dec - 2 Dec
includes taxes & fees
6.8/10 (1,006 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 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, 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 484 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.

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