Chesterfield Packages (Flight + Hotel)

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Top hotels in Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

3 out of 5
15431 Conway Rd Chesterfield MO
The price is ฿3,873 per night from 21 Jul to 22 Jul
฿3,873
฿4,492 total
21 Jul - 22 Jul
includes taxes & fees
8/10 Very good! (1,040 reviews)
"The only reason(s) im not leaving a 5 star review is because the walls & windows are super thin that you can easily hear the birds & the cars & if youre even 2 buildings from the pool, you can hear all the excitement from everyone. Im a light sleeper, so that may not be anyone else's concern. The ..."

Reviewed on 29 Jun 2026

Sonesta ES Suites St. Louis - Chesterfield
Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

3 out of 5
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
The price is ฿4,539 per night from 12 Jul to 13 Jul
฿4,539
฿5,265 total
12 Jul - 13 Jul
includes taxes & fees
9.6/10 Exceptional! (1,202 reviews)
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Reviewed on 29 Jun 2026

Drury Plaza Hotel 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 ฿5,488 per night from 17 Jul to 18 Jul
฿5,488
฿6,472 total
17 Jul - 18 Jul
includes taxes & fees
8.6/10 Excellent! (4,182 reviews)
"Clean room with excellent and helpful staff"

Reviewed on 30 Jun 2026

Hyatt Regency St. Louis at The Arch
See all 2,263 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.

Stay near popular Chesterfield attractions

St. Louis Premium Outlets

8.8/10 (369 reviews)
You can find the perfect gifts to bring home at St. Louis Premium Outlets during your stay in Chesterfield. Discover the top-notch restaurants and great live music in this family-friendly area.
See properties

What to do in Chesterfield

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

฿1,051
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
St. Louis Premium Driving Tour with Boat Ride & Arch

St. Louis Premium Driving Tour with Boat Ride & Arch

฿5,716
per adult
100% of travellers recommend
St. Louis Premium Driving Tour with Boat Ride & Arch
Best of St. Louis Small Group Tour w/ Arch & River Cruise

St. Louis Premium Small Group Tour With Arch & River Cruise

฿5,274
per adult
84% of travellers recommend
St. Louis Premium Small Group Tour With Arch & River Cruise
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.

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