Chesterfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Michelle E

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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$181 per night from 20 Aug to 21 Aug
NZ$181
20 Aug - 21 Aug
includes taxes & fees
8/10 Very Good! (1,005 reviews)
"We enjoyed the property"

Reviewed on 1 Aug. 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$233 per night from 7 Sept to 8 Sept
NZ$233
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"The room was clean and comfortable. The staff was friendly and helpful."

Reviewed on 5 Aug. 2025

Hyatt Place St. Louis/Chesterfield
Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4 out of 5
315 Chestnut St, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 22 Aug to 23 Aug
NZ$202
22 Aug - 23 Aug
includes taxes & fees
8.4/10 Very Good! (3,911 reviews)
"Proximity to the Arch is amazing."

Reviewed on 6 Aug. 2025

Hyatt Regency St. Louis at The Arch
See all 2,101 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.

Discover the most popular places to visit in Chesterfield

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
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
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

Adventure Valley Paintball Fun

Adventure Valley Paintball Park

NZ$19
per adult
Adventure Valley Paintball Park
St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

NZ$37
per adult
96% of travellers recommend
St Louis: City Museum General Admission Ticket
The Dinner Detective Murder Mystery Dinner Show - St. Louis

Dinner Detective True Crime Murder Mystery Show - St. Louis, MO

NZ$148
per adult
Dinner Detective True Crime Murder Mystery Show - St. Louis, MO
See all activities in Chesterfield

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.

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