Chesterfield Vacations from $339
Book a Hotel + Flight or Car together to unlock savings
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.
Remodeled and Inviting Free EV
$535
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
10/10 Exceptional! (1 review)
It was nice to stay for a weekend but the neighborhood was nice I like the location where it wasn't too far from grocery stores food areas the only thing I was saying is it's nothing for the kids to do but overall I like it
Reviewed on Aug 7, 2026
The Cheshire
$500
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
We had requested a refrigerator the first night at the hotel and told us they would get us one each day from 8/11 thru 8/13 and we checked out on 8/14. We lost a lot of perishable items because of this. Everyday we would ask and we told we would have it that day. It never happened. We were very disappointed.
Reviewed on Aug 18, 2026
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View all tripsStay 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.
St. Louis Premium Outlets
8.8/10 (369 reviews)
You can enjoy retail therapy at St. Louis Premium Outlets during your stay in Chesterfield. Discover the top-notch restaurants and great live music in this family-friendly area.
Sophia M. Sachs Butterfly House
8.8/10 (72 reviews)
Step into a tropical paradise where over 1,500 butterflies flutter freely through an 8,000-square-foot glass conservatory. Morning visits offer the best chance to witness these delicate creatures at their most active.
Babler State Park
8.6/10 (59 reviews)
This 2,500-acre natural haven offers miles of forest trails through scenic Ozark landscapes. Explore limestone valleys, spot native wildlife, and enjoy camping under the stars in Missouri's tranquil wilderness.
St. Louis Carousel
This century-old St. Louis Carousel features 60+ hand-carved wooden horses and deer in a climate-controlled pavilion. Enjoy nostalgic organ music while admiring the intricate craftsmanship of this rare antique treasure.
Topgolf
This high-tech golf venue blends precision tracking technology with casual fun for all skill levels. Enjoy climate-controlled hitting bays while savoring chef-prepared dishes delivered to your game area.
Dr. Edmund A. Babler Memorial State Park
8.2/10 (57 reviews)
You can take time to visit Dr. Edmund A. Babler Memorial State Park during your travels to Chesterfield. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Taubman Prestige Outlets
8.4/10 (81 reviews)
During your trip to Chesterfield, you can search for that perfect souvenir at Taubman Prestige Outlets. Discover the top-notch restaurants and great live music in this family-friendly area.
What to do in Chesterfield
St. Louis Ghost Tour: Sinister Sins & Shadows
$24
per adult
100% of travellers recommend
StL's Signature "Sights and Bites" - Private Tour in St. Louis
$175
per adult
Lemp Haunted Neighborhood Walking Tour
$25
per adult
84% of travellers recommend
Chesterfield Hotel Deals
Drury Plaza Hotel St. Louis Chesterfield
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
$130 nightly
$151 total
Aug 30 - Aug 31
Total with taxes and fees
Sonesta ES Suites St. Louis - Chesterfield
15431 Conway Rd Chesterfield MO
Fully refundableReserve now, pay when you stay
$105 nightly
$122 total
Aug 26 - Aug 27
Total with taxes and fees
8/10 Very Good! (1,042 reviews)
"Hotel needs some updates. The pool doesn’t have a light so when the sun goes down, you can’t see anything. The breakfast was terrible and waited 30 mins for pancakes. Stains on the carpet."
Reviewed on Aug 17, 2026
Holiday Inn Express & Suites St. Louis - Chesterfield by IHG
11 Arnage Boulevard Chesterfield MO
Fully refundable
$114 nightly
$133 total
Aug 30 - Aug 31
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"Had requested a king bed. The bed had a large hole on one side. We told the office staff and requested another bed. Were told none were available, but, would see if it could be repaired. The last night of our stay Gus helped us get into another room. He was very helpful, but it was the last night ..."
Reviewed on Aug 17, 2026
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 |
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Frequently asked questions
How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from $339 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?
- Choose your dates: The things you want to do in Chesterfield and your preferred season will help you decide when to go.
- 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.
- 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.
- 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.
- 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.
- 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.
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- St. Louis Premium Outlets
- Meeting of the Waters Fountain
- St. Louis Art Museum
- Ballwin Vacations
- St. Louis Cathedral
- Creve Coeur Vacations
- St. Louis Vacations
- American Kennel Club Museum of the Dog
- Hollywood Casino Amphitheatre
- Citygarden
- Grant's Farm
- Chaifetz Arena
- Six Flags St. Louis
- Myseum
- St. Louis Zoo
- Museum at the Gateway Arch
- Hidden Valley Ski Resort
- The MOTO Museum
- Eads Bridge
- Hollywood Casino
- Missouri Botanical Gardens and Arboretum
- Magic House - St. Louis Children's Museum
- August A. Busch Memorial Conservation Area
- Dr. Edmund A. Babler Memorial State Park
- The Muny Theater
- Missouri Bluffs Golf Course
- Old Post Office
- Kokomo Joe's Family Fun Center
- Christ Church Cathedral
- Downtown St. Louis Vacations
- Visit St. Louis
- St. Mary of Victories Catholic Church
- St. Alphonsus Liguori Catholic Church
- Bruno David Gallery
- Lone Elk Park
- St. Louis Science Center
- Historic Aircraft Restoration Museum
- Wainwright Building
- Eugene Field House & St. Louis Toy Museum
- Jewel Box
- Citygarden Sculpture Park
- Samuel Cupples House
- Sky Zone Indoor Trampoline Park - St. Louis
- Museum of Transportation
- Gateway Arch
- Westport Plaza
- Lou Fusz Soccer Complex
- Laumeier Sculpture Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.