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Our top choices for Chesterfield hotels

Lobby
Hotel UMass

Hotel UMass

2.5 star property
Amherst
8.8 out of 10, Excellent, (1001)
"Great on campus location!"
United States
Shuhui
The price is NZ$245
includes taxes & fees
21 Dec - 22 Dec
Hotel UMass
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is NZ$187
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Balcony
Inn on Boltwood

Inn on Boltwood

3.0 star property
Amherst
9.4 out of 10, Exceptional, (748)
"Room was clean and the bed was very comfortable. "
United States
Michael
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, (794)
"Staff are awesome"
United States
Sherry
The price is NZ$166
includes taxes & fees
14 Dec - 15 Dec
Candlewood Suites West Springfield by IHG
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, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NZ$178
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Clean room and staff was super friendly"
United States
Yuen
The price is NZ$288
includes taxes & fees
11 Dec - 12 Dec
Hotel On North
Basic Studio, 1 King Bed
River Valley Inn

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (98)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is NZ$211
includes taxes & fees
11 Dec - 12 Dec
River Valley Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (785)
"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, (1002)
"Great like always "
United States
Sharee
The price is NZ$168
includes taxes & fees
23 Dec - 24 Dec
Red Roof Inn PLUS+ West Springfield
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2241)
"Comfortable beds, good bedding, good shower, decent hot breakfast."
Canada
Robert
The price is NZ$220
includes taxes & fees
2 Jan - 3 Jan 2026
D. Hotel Suites & Spa
Property amenity
Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

3.0 star property
Hadley
9.0 out of 10, Wonderful, (681)
"Nice and quiet and conveniently located very close to UMass"
United States
Connor
The price is NZ$277
includes taxes & fees
21 Dec - 22 Dec
Courtyard by Marriott Hadley Amherst
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, (1003)
"Room and staff were good "
United States
George
The price is NZ$154
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn West Springfield
Lobby
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
Northampton
9.2 out of 10, Wonderful, (1001)
"An excellent stay. Wonderfully clean, friendly front desk staff and the breakfast buffet was actually good. Will definitely stay again."
United States
Joyce
The price is NZ$242
includes taxes & fees
28 Dec - 29 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, (580)
"Room was clean and staff was super friendly "
United States
Jessuca
The price is NZ$234
includes taxes & fees
18 Dec - 19 Dec
Courtyard by Marriott West Springfield
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 star property
Lee
8.4 out of 10, Very good, (1001)
"Clean room and good breakfast "
United States
Kelly
The price is NZ$175
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Lee - Lenox South
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, (102)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is NZ$234
includes taxes & fees
29 Dec - 30 Dec
Blue – A Modern Hotel, an Ascend Collection Hotel
Lobby
Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

2.5 star property
Hadley
9.2 out of 10, Wonderful, (1010)
"Room was spotless and the amenities were great. "
United States
kathleen
The price is NZ$239
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Hadley - Amherst
Lobby
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 star property
West Springfield
8.2 out of 10, Very good, (1000)
"nearby eateries"
United States
Majorie
The price is NZ$189
includes taxes & fees
15 Dec - 16 Dec
Hampton Inn West Springfield
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, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NZ$173
includes taxes & fees
11 Dec - 12 Dec
The Central Downtown 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 NZ$155
includes taxes & fees
24 Dec - 25 Dec
FairBridge Inn Express
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

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

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"Well maintained hotel with a friendly staff. I was very surprised how clean and quiet the hotel was. Book this place! I’ll definitely stay here again when in the area."
Jaime 3-night trip
Posted 1 day ago
Blue – A Modern Hotel, an Ascend Collection Hotel

More cheap accommodation in Chesterfield

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
The price is NZ$154 per night from 4 Jan to 5 Jan
NZ$154
4 Jan - 5 Jan 2026
includes taxes & fees
7/10 Good! (1,002 reviews)

Frequently asked questions

Where is the best place to stay in Chesterfield?
Located 14.5 mi (23.3 km) from the heart of Chesterfield, D. Hotel Suites & Spa is a top choice for your stay, based on our traveller data. Two other choices for your visit to the area are Berkshire Mountain Lodge and Quality Inn West Springfield. See all available top hotels, or vacation rentals in Chesterfield.
What are some of the best holiday rentals that Chesterfield has to offer?
Peace and quiet on the lake: This holiday home rental outside of Chesterfield is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most 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, 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 483 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, Knightville Dam & Reservation and Westfield River. 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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