Chesterfield Holidays
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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.
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$206 per night from 26 Jan to 27 Jan
AU$206
26 Jan - 27 Jan
includes taxes & fees
9.2/10 Wonderful! (2,226 reviews)
Was just there for a short overnight stay but room was comfortable clean, fixtures in good shape, service front desk was professional.
Reviewed on 17 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 1 Feb to 2 Feb
AU$197
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (813 reviews)
Wonderful night!! Staff go out of their way to help you!!
Reviewed on 17 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is AU$163 per night from 23 Jan to 24 Jan
AU$163
23 Jan - 24 Jan
includes taxes & fees
8/10 Very Good! (1,006 reviews)
generally good
Reviewed on 19 Jan 2026
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.
