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Cheap Chesterfield hotels

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 1 Jan to 2 Jan
AU$191
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at D. Hotel Suites & Spa in Holyoke, you'll be 4.6 mi (7.4 km) from Smith College and 10.4 mi (16.7 km) from University of Massachusetts ...
Opens in a new windowD. Hotel Suites & Spa
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is AU$156 per night from 16 Dec to 17 Dec
AU$156
16 Dec - 17 Dec
includes taxes & fees
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AU$199 per night from 8 Jan to 9 Jan
AU$199
8 Jan - 9 Jan 2026
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Opens in a new windowBerkshire Mountain Lodge
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Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 21 Dec to 22 Dec
AU$203
21 Dec - 22 Dec
includes taxes & fees
When you stay at Courtyard by Marriott West Springfield in West Springfield, you'll be near the airport, within a 5-minute drive of Big E and Baystate Medical ...
Opens in a new windowCourtyard by Marriott West Springfield
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
400 Russell St Hadley MA
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 28 Dec to 29 Dec
AU$207
28 Dec - 29 Dec
includes taxes & fees
With a stay at Comfort Inn & Suites Hadley - Amherst in Hadley, you'll be within a 5-minute drive of University of Massachusetts Amherst and Autobahn.
Opens in a new windowComfort Inn & Suites
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 22 Dec to 23 Dec
AU$149
22 Dec - 23 Dec
includes taxes & fees
With a stay at Tru by Hilton Chicopee Springfield in Chicopee, you'll be within a 10-minute drive of MassMutual Center and MGM Springfield.
Opens in a new windowTru by Hilton Chicopee Springfield
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 4 Jan to 5 Jan
AU$134
4 Jan - 5 Jan 2026
includes taxes & fees
In the heart of West Springfield, Quality Inn West Springfield is within a 5-minute drive of Big E and Olympia Ice Center.
Opens in a new windowQuality Inn West Springfield
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
Fully refundable
The price is AU$203 per night from 4 Jan to 5 Jan
AU$203
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Blue – A Modern Hotel, an Ascend Collection Hotel, you'll be centrally located in West Springfield, within a 10-minute drive of MassMutual Center ...
Opens in a new windowBlue – A Modern Hotel, an Ascend Collection Hotel
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
Fully refundableReserve now, pay when you stay
With a stay at Hotel Northampton, you'll be centrally located in Northampton, within a 15-minute drive of University of Massachusetts Amherst and Calvin ...
Opens in a new windowHotel Northampton
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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.

Hotels in Chesterfield

Searching for a hotel in Chesterfield, United States of America? Unfortunately, you won't find a whole lot of places to crash right within close reach. But take a short drive out and you'll enjoy more choice than you can shake your room-booking index finger at. There are 33 different accommodation options within 30 kilometres of Chesterfield's centre, so you'll be able to find the ideal digs for you.

Once you've crossed off your must sees for the day, your fluffy gown and slippers are waiting at Hotel Northampton or Naomi's Inn Bed & Breakfast. Alternatively, have a look at the Residence Inn by Marriott West Springfield and the Hampton Inn & Suites Greenfield.

Just 20 kilometres from the centre streets is Northampton. This neighbourhood has 5 hotels and accommodations. Want to know our recommended picks? Start off by looking at the Clarion Hotel & Conference Center and Quality Inn & Suites Northampton-Amherst.

After more options? The Old Mill Inn can be found 20 kilometres away from the downtown area, and the Homewood Suites by Hilton Holyoke-Springfield/North is 30 kilometres away. The Hampton Inn Hadley/Amherst area, 20 kilometres away, and the Hampton Inn West Springfield, 35 kilometres away, are some alternate choices.

Lee is another place where you can sit back and order up some room service like a boss. Sitting 35 kilometres west of Chesterfield, it's where you'll discover the Tanglewood Music Center and Tyringham Cobble. If you want to spend a few nights in Lee, look into the rates at the Cranwell Spa and Golf Resort and Federal House Inn. 35 kilometres to the west of Chesterfield you'll also find Pittsfield, home to the Crowne Plaza Pittsfield-Berkshires and White Horse Inn. Whether you're just passing through or staying in Pittsfield, be sure to explore the Crane Museum of Papermaking and the Skyline Country Club.

Go 35 kilometres west and you'll find Lenox, a regional centre with a population of 2,000. While you're checking out this neck of the woods, whip out your selfie stick and get your tourist on at the Berkshire Scenic Railway Museum, the Cranwell Golf Club and Kennedy Park. Ventfort Hall Mansion and Gilded Age Museum and the Shakespeare and Company are a couple more attractions which are sure to offer up some envy-inducing photo ops. There are a range of great hotels where you can hit the hay for a night or two in Lenox. We recommend checking out the deals at the Gateways Inn & Restaurant and Hampton Terrace Inn.

Just landed at Bradley International Airport? Feeling a bit icky after the flight? Not a problem. Towels and soap are up for grabs nearby at the Sheraton Hartford Hotel at Bradley Airport. If you can't snap up a room there, try your luck at the Holiday Inn Express & Suites Bradley Airport. It's also nice and close to the airport, which sits 50 kilometres from Chesterfield's centre.

Chesterfield hotels essential information

Accommodation
487 hotels
Lowest Price
AU$134
Highest Price
AU$207
Popular hotels
D. Hotel Suites & Spa, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshire Mountain Lodge, Courtyard by Marriott West Springfield, Comfort Inn & Suites, Tru by Hilton Chicopee Springfield, Quality Inn West Springfield, Blue – A Modern Hotel, an Ascend Collection Hotel, Hotel Northampton

Most recent Chesterfield hotel reviews

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