Find hotels in Chesterfield, MA from ₩109,219

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Nov 7 - Nov 8
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Compare 482 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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 ₩141,339
₩157,877 total
includes taxes & fees
Dec 5 - Dec 6
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
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 ₩141,339
₩161,762 total
includes taxes & fees
Nov 19 - Nov 20
Candlewood Suites West Springfield 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, (56)
"Bright new hotel with very friendly and helpful staff. "
United States
Mary
The price is ₩170,399
₩190,336 total
includes taxes & fees
Dec 7 - Dec 8
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
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 ₩171,625
₩191,706 total
includes taxes & fees
Nov 17 - Nov 18
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
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 ₩122,013
₩139,645 total
includes taxes & fees
Dec 7 - Dec 8
Red Roof Inn PLUS+ West Springfield
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 ₩193,219
₩215,825 total
includes taxes & fees
Nov 16 - Nov 17
Hotel On North
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 ₩129,065
₩147,715 total
includes taxes & fees
Nov 16 - Nov 17
Quality Inn West Springfield
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 ₩192,552
₩216,692 total
includes taxes & fees
Dec 7 - Dec 8
Hotel UMass
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 ₩97,776
₩109,219 total
includes taxes & fees
Nov 23 - Nov 24
FairBridge Inn Express
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 ₩194,104
₩216,815 total
includes taxes & fees
Nov 23 - Nov 24
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 ₩158,141
₩180,992 total
includes taxes & fees
Dec 7 - Dec 8
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, (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 ₩158,496
₩184,121 total
includes taxes & fees
Nov 17 - Nov 18
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 ₩170,399
₩195,022 total
includes taxes & fees
Dec 7 - Dec 8
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 ₩195,770
₩218,676 total
includes taxes & fees
Nov 30 - Dec 1
Courtyard by Marriott Hadley Amherst
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 ₩163,044
₩182,110 total
includes taxes & fees
Nov 18 - Nov 19
The Central Downtown Inn & Suites
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 ₩126,573
₩141,381 total
includes taxes & fees
Dec 1 - Dec 2
Quality Inn
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 ₩182,226
₩203,546 total
includes taxes & fees
Nov 30 - Dec 1
Comfort Inn & Suites
Desk, laptop workspace, blackout drapes, 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 ₩123,297
₩137,722 total
includes taxes & fees
Nov 17 - Nov 18
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 forest 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

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

10/10 Excellent
"Parking was easy and secure. A/C kept the room comfortable."
Jerry Mark 1-night trip
Posted 4 days ago
Red Roof Inn PLUS+ South Deerfield – Amherst

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 ₩122,013 per night from Dec 7 to Dec 8
₩122,013
₩139,645 total
Dec 7 - Dec 8
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 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.
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.

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