Chesterfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Michelle E

Top hotels in 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 3.505.374 ₫ per night from 3 Aug to 4 Aug
3.505.374 ₫
4.065.814 ₫ total
3 Aug - 4 Aug
includes taxes & fees
9.4/10 Exceptional! (1,012 reviews)
"Everything was great."

Reviewed on 27 Jul 2025

Hyatt Place St. Louis/Chesterfield
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 2.425.792 ₫ per night from 3 Aug to 4 Aug
2.425.792 ₫
2.813.627 ₫ total
3 Aug - 4 Aug
includes taxes & fees
8/10 Very Good! (1,021 reviews)
"breakfast same every day and boring"

Reviewed on 27 Jul 2025

Sonesta ES Suites 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 2.799.594 ₫ per night from 22 Aug to 23 Aug
2.799.594 ₫
3.301.533 ₫ total
22 Aug - 23 Aug
includes taxes & fees
8.4/10 Very Good! (3,886 reviews)
"Very clean"

Reviewed on 25 Jul 2025

Hyatt Regency St. Louis at The Arch
See all 2,098 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.

Popular places to visit

St. Louis Union Station

St. Louis Union Station

4.5/5(4 reviews)

You can learn more about the history of St. Louis during your trip to a well-known site such as St. Louis Union Station. Experience the area's acclaimed art galleries or attend a baseball game.

St. Louis Union Station
Gateway Arch showing a city, city views and skyline

Gateway Arch

5/5(16 reviews)

Find out about the history of Gateway Arch, one of the top monuments in St. Louis. Experience the area's acclaimed art galleries or attend a baseball game.

Gateway Arch
St. Louis Zoo

St. Louis Zoo

Why not visit the animals who live at St. Louis Zoo and see why this is a favourite attraction in St. Louis? Amble around the area's lush forest or attend a sporting event.

St. Louis Zoo

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.