Chesterfield Holidays from AU$2,359

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

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

    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.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was AU$3,150, price is now AU$2,359 per person
AU$2,359
per person
28 Oct - 2 Nov
just found
Return flight included
Sydney (SYD) to Boston (BOS)
9/10 Wonderful! (2,711 reviews)
“The air conditioning was not working properly and was extremely loud. The bathroom door did not close properly, and the room felt very outdated.”

Reviewed on 25 Aug. 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was AU$6,112, price is now AU$4,429 per person
AU$4,429
per person
2 Oct - 6 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on 24 Aug. 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was AU$3,649, price is now AU$2,684 per person
AU$2,684
per person
28 Oct - 2 Nov
just found
Return flight included
Sydney (SYD) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Super comfortable beds and a great location. A joy to stay in!

Reviewed on 24 Aug. 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
Price was AU$3,768, price is now AU$2,784 per person
AU$2,784
per person
28 Oct - 2 Nov
just found
Return flight included
Sydney (SYD) to Boston (BOS)
9.2/10 Wonderful! (1,326 reviews)
Nos encanta este hotel y siempre volvemos.

Reviewed on 24 Aug. 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was AU$4,295, price is now AU$3,198 per person
AU$3,198
per person
28 Oct - 2 Nov
just found
Return flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (441 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on 16 Aug. 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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (589 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."

Reviewed on 23 Aug. 2025

Get rates
Berkshire Mountain Lodge
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$220 per night from 1 Sept to 2 Sept
AU$220
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,219 reviews)
"Clean hotel, large room, comfortable bed, great breakfast"

Reviewed on 24 Aug. 2025

D. Hotel Suites & Spa
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$156 per night from 7 Sept to 8 Sept
AU$156
7 Sept - 8 Sept
includes taxes & fees
7/10 Good! (1,002 reviews)
"."

Reviewed on 18 Aug. 2025

Quality Inn West Springfield
See all 466 properties in Chesterfield
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chesterfield holiday package cost?
You'll find cheap prices from AU$2,359 on Expedia for your Chesterfield getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your holiday to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
You can usually find reduced prices and greater availability in January, February and November. Browse our cheap Chesterfield holiday packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-organised travel plan, you can easily visit the top Chesterfield sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your Chesterfield holiday for longer.
How to find the best Chesterfield package deals?
Landing a cheap Chesterfield package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Chesterfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesterfield holiday as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalised holiday package. Click on the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Chesterfield?
If you have your Chesterfield holiday dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Chesterfield?

  1. Pick your dates: The things you'd like to do in Chesterfield and your preferred season will help you decide when to get away.
  2. Budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Chesterfield.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Chesterfield. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodation and airfare: After you've settled on your travel dates and duration, book the right Chesterfield holiday package for you.

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