Chesterfield Vacations from $139

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Chesterfield Vacation

Let our vacation packages to Chesterfield inspire your next great escape. There's a whole lot to love about this amazing city, starting with the neighborhood of Valley Park, which is great for golfing and nature. Make your trip to Chesterfield even more enjoyable by going sightseeing. St. Louis Premium Outlets, Lou Fusz Soccer Complex and Westfield Chesterfield Mall are some of the leading attractions worth exploring. Whatever your travel plans or budget, organizing a tailored Chesterfield vacation is a cinch with Expedia.

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn St. Louis Arpt West-Earth City by IHG

Holiday Inn St. Louis Arpt West-Earth City by IHG

3.5 out of 5
Price was $185, price is now $139 per person
$139
per person
Dec 19 - Dec 21
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
7.6/10 Good! (1,001 reviews)
It was clean and have no complaints.

Reviewed on Nov 3, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $354, price is now $177 per person
$177
per person
Dec 19 - Dec 21
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,677 reviews)

Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Price was $662, price is now $423 per person
$423
per person
Jan 8 - Jan 11
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.4/10 Exceptional! (3 reviews)
We had a great time with my family ❤️ thank you

Reviewed on Oct 12, 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was $595, price is now $445 per person
$445
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,080 reviews)

The Cheshire

The Cheshire

4 out of 5
Price was $531, price is now $405 per person
$405
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)
The Cheshire Inn is such a great, unique hotel - we loved our first stay here! We came in for WashU parents' weekend and stayed two nights. Very well-appointed hotel, super cute decorations and theme, very clean and tidy. The bar is a nice spot for a cocktail or draft beer and the lobby and sitting areas are spacious and comfy. Free breakfast was a very nice amenity. We very much look forward to staying at the Cheshire again in the future!

Reviewed on Nov 3, 2026

Don't see what you're looking for?
See all available trips from Boydton to Chesterfield
View all trips

Stay near popular Chesterfield attractions

The Factory

8.8/10 (47 reviews)
The Factory hosts a diverse range of concerts in an intimate yet spacious setting with excellent acoustics. Arrive early to explore this modern venue with comfortable seating and multiple bars before performances begin.
See properties

What to do in Chesterfield

The Gateway Arch National Park & Museum

StL's Signature "Sights and Bites" - Private Tour in St. Louis

$175
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

$24
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
Self-Guided Audio Tour of Gateway Arch National Park & St. Louis

Self-Guided Audio Tour of Gateway Arch National Park & St. Louis

$15
per traveler
Self-Guided Audio Tour of Gateway Arch National Park & St. Louis
See all activities in Chesterfield

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
$93 nightly
The price is $107 total per night from Nov 8 to Nov 9
$107 total
Nov 8 - Nov 9
Total with taxes and fees
8/10 Very Good! (1,064 reviews)
"Very nice place spacious rooms. Accessible and very accommodating..Will return"

Reviewed on Nov 3, 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
$130 nightly
The price is $151 total per night from Nov 8 to Nov 9
$151 total
Nov 8 - Nov 9
Total with taxes and fees
Drury Plaza Hotel 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
$121 nightly
The price is $140 total per night from Nov 8 to Nov 9
$140 total
Nov 8 - Nov 9
Total with taxes and fees
9.6/10 Exceptional! (1,009 reviews)
"Very nice hotel and lovely room"

Reviewed on Nov 4, 2026

Hyatt Place St. Louis/Chesterfield
See all 2,300 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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
47,900
Max Temp Winter
40ºF
Max Temp Summer
90ºF
Top Sights
Six Flags St. Louis, Magic House - St. Louis Childrens Museum and Route 66 State Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from $139 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. Opting to travel in quieter months means you'll typically find better prices on flights and hotels.
How many days is enough for Chesterfield?
Chesterfield vacations can be short or long, but to really sink your teeth into this destination, we'd say 2 days is about right. This will mean you can fit in headline attractions like Myseum and Sophia M. Sachs Butterfly House along with underrated spots. Don't forget to visit cool neighborhoods such as Clarkson Valley and Winchester either. If you're smart with your time, you can even schedule a day trip or two from Chesterfield too.
Is it worth booking a vacation package to Chesterfield?
Well known for its golfing, nature and shopping, a Chesterfield vacation is a hit with all kinds of travelers. Be sure to visit leading sights like Chesterfield Sports Fusion and Westfield Chesterfield Mall, and consider renting some wheels for day trips to explore even more.
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: The things you want to do in Chesterfield and your preferred season will help you decide when to go.
  2. Set your budget: Factor in costs like food, flights and transportation when working out how much to set aside for your trip to Chesterfield. Then, select a property that matches your budget, whether that's an economical stay or a lavish retreat.
  3. Use our trip planning tool to explore Chesterfield: Research every aspect of your trip to Chesterfield with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by making a list of all the sights and activities you'd like to experience in Chesterfield. Then, estimate how long you'll need at each, including any travel time.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Chesterfield vacation package that brings all your bookings together.
  6. Book any activities or day trips: Now to the fun part — organizing everything you want to see and do. Browse some of the top things to do in Chesterfield in Chesterfield and book your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Your Chesterfield trip should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

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