Chesterfield Holidays from AU$577
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Your Chesterfield Holiday
Our Chesterfield holiday packages offer endless opportunities to delve into new sights, sounds and experiences. And with all your travel plans taken care of, you can kick back and enjoy your city getaway to the fullest. If your trip to Chesterfield includes some sightseeing, take in famous attractions like Chesterfield Gorge, Swift River and Petticoat Hill. Browse Expedia's extensive range of travel options and start organising your dream holiday to Chesterfield today.
The Latest Chesterfield Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay
Back Bay
Price was AU$987, price is now AU$709 per person
AU$709
per person
9 Jan - 11 Jan
found 1 day ago
Return flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Hidden gem in Boston - central location, spotless rooms, surprisingly affordable rates compared to similar properties, and standout guest relations staff with a level of attentiveness and top-shelf service worthy of any five-staff hotel. Truly above and beyond.
Reviewed on 3 Dec 2025
Chesterfield Holiday
Chesterfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,200 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Academy of Music Theatre, Calvin Theatre and Historic Northampton |
Our pick of the best Chesterfield Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 8 Dec to 9 Dec
AU$151
8 Dec - 9 Dec
includes taxes & fees
9.2/10 Wonderful! (2,273 reviews)
The hotel was great. The biggest thing keeping this from being excellent was that the thermostat in the room didn't work. The fan was set to auto yet the heater kept heating until it was too hot. We had to turn it off at times and it made sleeping uncomfortably hot.
Reviewed on 29 Nov 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (776 reviews)
Friendly staff, room was very clean. Pool area well maintained. Overall a great place to stay
Reviewed on 30 Nov 2025
Comfort Inn & Suites
400 Russell St Hadley MA
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 28 Dec to 29 Dec
AU$210
28 Dec - 29 Dec
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
Everything was clean and staff was excellent.
Reviewed on 30 Nov 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
