Chesterfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Michelle E

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to NZ$616 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

Chesterfield Holiday

Our pick of the best Chesterfield Hotel Deals

Sonesta ES Suites St. Louis - Chesterfield
Sonesta ES Suites St. Louis - Chesterfield
3 out of 5
15431 Conway Rd, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is NZ$180 per night from 1 July to 2 July
NZ$180
1 July - 2 July
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Clean and comfy. The suite was very nice."

Reviewed on 19 Jun. 2025

Sonesta ES Suites St. Louis - Chesterfield
Hyatt Place St. Louis/Chesterfield
Hyatt Place St. Louis/Chesterfield
3 out of 5
333 Chesterfield Center East, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is NZ$237 per night from 21 July to 22 July
NZ$237
21 July - 22 July
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Nice and clean. Friendly service."

Reviewed on 19 Jun. 2025

Hyatt Place St. Louis/Chesterfield
Homewood Suites by Hilton St. Louis-Chesterfield
Homewood Suites by Hilton St. Louis-Chesterfield
3 out of 5
840 North Chesterfield Pkwy West, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is NZ$259 per night from 3 July to 4 July
NZ$259
3 July - 4 July
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Very nice and friendly staff with a well kept room amd lobby."

Reviewed on 19 Jun. 2025

Homewood Suites by Hilton St. Louis-Chesterfield
See all 2,067 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.

Frequently asked questions

How much does a Chesterfield holiday package cost?
You can pick up a holiday package to this top destination on Expedia. But how much your holiday to Chesterfield costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chesterfield?
December, January and February are great times to search for cheap Chesterfield holiday packages. Travelling in less busy periods means you'll typically find reduced prices on accommodation and flights.
How many days is enough for Chesterfield?
With about 2 days, you'll have plenty of time to enjoy popular neighbourhoods such as Clarkson Valley and Winchester during your Chesterfield holiday. Be sure to also add Myseum and The Factory to your sightseeing itinerary. In the mood for more adventures? Consider exploring outside of Chesterfield on day trips and tours.
Is it worth booking a holiday package to Chesterfield?
Chesterfield has all the ingredients you need for an amazing break --- golfing, nature and shopping are just the start. Whether you'd like to check out sights like The Factory and Chesterfield Sports Fusion, or venture off the beaten track, you'll have plenty to do on your Chesterfield holiday.
How to find the best Chesterfield package deals?
Begin your search for a Chesterfield package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesterfield package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chesterfield adventure underway.
Is it cheaper to book a Chesterfield holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a customised Chesterfield holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Chesterfield?
If you've got your Chesterfield travel dates finalized, book as early as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Chesterfield?

  1. Choose your dates: What you plan to do in Chesterfield and your favourite season can help you decide when to get away.
  2. Set a budget: Consider expenses like transportation, flights and meals when calculating how much to set aside for your trip to Chesterfield. Then, choose a hotel that works with your budget, whether that's an affordable option or a high-end retreat.
  3. Decide your trip length: Think about how long you'd like to spend exploring Chesterfield. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodation: After you've settled on your travel dates and duration, book the right Chesterfield holiday package for you.

Discover the most popular places to visit in Chesterfield

St. Louis Zoo

St. Louis Zoo

4/5(1 review)

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

St. Louis Zoo
Gateway Arch which includes skyline, a city and modern architecture

Gateway Arch

4.5/5(9 reviews)

Climb to the very top of America’s tallest man-made structure for sweeping views across the city of St. Louis and the surrounding countryside.

Gateway Arch
City Museum which includes a city as well as children

City Museum

3/5(1 review)

Leave all expectations at the door and let yourself be swept along by the weird, wacky and wildly exciting at this singular museum experience.

City Museum

What to do in Chesterfield

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

NZ$37
per adult
94% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis Arch Walking Tour and Entrance Ticket

St. Louis Arch Walking Tour and Entrance Ticket

NZ$83
per adult
St. Louis Arch Walking Tour and Entrance Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis: Gateway Ghouls and Hauntings Walking Tour

NZ$53
per adult
St. Louis: Gateway Ghouls and Hauntings Walking Tour
See all activities in Chesterfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.