Chesterfield Holidays from AU$1,071

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Battery Wharf Hotel, Boston Waterfront
The Whitney Hotel
The Langham, Boston
The Newbury Boston
XV Beacon

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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$195 per night from 2 Nov to 3 Nov
AU$195
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (716 reviews)
"Yes, everything was very well set up. Thanks."

Reviewed on 19 Oct 2025

Berkshire Mountain Lodge
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$159 per night from 16 Nov to 17 Nov
AU$159
16 Nov - 17 Nov
includes taxes & fees
7/10 Good! (1,019 reviews)
Great hotel for a cheap night passing through town
"Over all great stay. Looking for a decent place to overnight traveling back home from a vacation. Check in process was easy and greeting immediately with a friendly staff member who appeared to be training but still very efficient at their job. We were giving directions to the elevators and went ..."

Reviewed on 13 Oct 2025

Quality Inn West Springfield
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$196 per night from 22 Oct to 23 Oct
AU$196
22 Oct - 23 Oct
includes taxes & fees
9.2/10 Wonderful! (2,252 reviews)
"We’ve stayed here every fall for the past 3 years, and will continue doing so. Suite is spacious, breakfast is good, employees are kind and respectful."

Reviewed on 17 Oct 2025

D. Hotel Suites & Spa
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.