Chesterfield Vacations from ￥390,218

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 ￥45,448 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

The Latest Chesterfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was ￥428,926, price is now ￥390,218 per person
￥390,218
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Osaka (ITM) to St. Louis (STL)
8.2/10 Very Good! (762 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul 26, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was ￥459,116, price is now ￥393,048 per person
￥393,048
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Osaka (ITM) to St. Louis (STL)
9.2/10 Wonderful! (1,561 reviews)
Always comfortable, always convenient and reliable when I'm visiting the area. It's my go-to hotel in the area.

Reviewed on Aug 25, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was ￥476,620, price is now ￥430,190 per person
￥430,190
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Osaka (ITM) to St. Louis (STL)
8.4/10 Very Good! (1,002 reviews)
Loved my stay here will be back

Reviewed on Aug 13, 2025

Seven Gables, St. Louis West, a Tribute Portfolio Hotel

Seven Gables, St. Louis West, a Tribute Portfolio Hotel

3.5 out of 5
Clayton
Price was ￥506,607, price is now ￥460,313 per person
￥460,313
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Osaka (ITM) to St. Louis (STL)
8.4/10 Very Good! (568 reviews)
Very quiet. Moved to the first floor. Room very nice. Elevator was out.

Reviewed on Aug 7, 2025

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was ￥444,812, price is now ￥404,552 per person
￥404,552
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Osaka (ITM) to St. Louis (STL)
9.4/10 Exceptional! (376 reviews)
Great location! Very convenient!

Reviewed on Aug 24, 2025

Find the Best Chesterfield Vacation Packages

Chesterfield Hotel Deals

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 ￥19,167 per night from Sep 9 to Sep 10
￥19,167
￥22,231 total
Sep 9 - Sep 10
includes taxes & fees
9.6/10 Exceptional! (1,011 reviews)
"Nice staff and service"

Reviewed on Aug 25, 2025

Drury Plaza Hotel 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 ￥12,828 per night from Sep 9 to Sep 10
￥12,828
￥14,879 total
Sep 9 - Sep 10
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"It has a nice lay out. Just needs some upkeep."

Reviewed on Aug 15, 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 ￥18,136 per night from Sep 25 to Sep 26
￥18,136
￥21,037 total
Sep 25 - Sep 26
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Good hotel"

Reviewed on Aug 21, 2025

Hyatt Place St. Louis/Chesterfield
See all 2,071 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

Busch Stadium

Busch Stadium

4.5/5(1,469 reviews)

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.

Busch Stadium
St. Louis Union Station

St. Louis Union Station

4/5(615 reviews)

You can learn about the local history of St. Louis when you make a stop at a well-known site like St. Louis Union Station. Experience the area's fascinating museums or attend a baseball game.

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

Gateway Arch

4.5/5(2,511 reviews)

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch

What to do in Chesterfield

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

￥3,293
per adult
96% 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

￥7,389
per adult
St. Louis Arch Walking Tour and Entrance Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

￥3,534
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from ￥390,218 on Expedia. But how much your vacation 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 vacation packages. Traveling in less busy periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Chesterfield?
With about 2 days, you'll have plenty of time to enjoy popular neighborhoods such as Clarkson Valley and Winchester during your Chesterfield vacation. 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 vacation 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 vacation.
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 vacation as a package?
Expedia vacation 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 customized Chesterfield vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation 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 favorite 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 accommodations: After you've settled on your travel dates and duration, book the right Chesterfield vacation package for you.

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