Chesterfield Vacations from $306
Book a Hotel + Flight or Car together to unlock savings
Photo by Michelle E
- Plan, book, travel with confidence
Better together
Save up to $1,045 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.
DoubleTree by Hilton Hotel St. Louis - Chesterfield
per person
Oct 24 - Oct 26
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,001 reviews)
Beautiful property, pleasant and responsive staff, delicious warm cookies! And convenient location near city hall and police department.
Reviewed on Jul 27, 2025
WorldMark Lake of the Ozarks
per person
Oct 31 - Nov 4
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
9.4/10 Exceptional! (400 reviews)
Great property! Your balcony view is directly on the water. This property offers a dock unused just for guests. I would bring your own raft or float to enjoy the water. The pools and hot tube area are nice, and offer grills for cooking in the pool area and another location.
Check in was great except our room wasn’t ready until 5, the check in time was 4, however they made accommodations to us to offset the delay. It’s close to many fun things to do at the Lake of the Ozarks!! We will be back and will stay here again.
Reviewed on Aug 10, 2025
Alhonna Resort LLC
per person
Oct 10 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to St. Louis (STL)
8.6/10 Excellent! (206 reviews)
The restaurant and bar had good food and drinks. There was a great band that played by the pool on Friday and Saturday...I met great people vacationing there and the front desk staff was helpful, cheerful, and welcoming!! This isn't my first time there and it won't be my last
Reviewed on Aug 15, 2025
Courtyard by Marriott St. Louis Downtown/Convention Center
Downtown St. Louis
per person
Oct 24 - Oct 26
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9/10 Wonderful! (1,004 reviews)
Valet greeted you at the door check in was quick and easy rooms were spacious and very clean
Reviewed on Aug 10, 2025
Camden on the Lake Resort & Spa
per person
Oct 10 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to St. Louis (STL)
9/10 Wonderful! (1,001 reviews)
Hotel was overall clean and staff were friendly and helpful. Enjoyed the lakeside pool and our room was very nice.
Reviewed on Aug 7, 2025
Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all tripsDiscover the most popular places to visit in Chesterfield
Busch Stadium
Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.
St. Louis Union Station
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.
Gateway Arch
Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.
What to do in Chesterfield
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
$32
per adult
Best of St. Louis Small Group Tour w/ Arch & River Cruise
$169
per adult
84% of travellers recommend
St. Louis: Guided Small Group City Tour with River Cruise
$174
per adult
100% of travellers recommend
Chesterfield Hotel Deals
Sonesta ES Suites St. Louis - Chesterfield
15431 Conway Rd, Chesterfield, MO
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $108 total per night from Aug 24 to Aug 25
$108 total
Aug 24 - Aug 25
Total includes taxes and fees
7.8/10 Good! (1,005 reviews)
"It has a nice lay out. Just needs some upkeep."
Reviewed on Aug 15, 2025
Hyatt Place St. Louis/Chesterfield
333 Chesterfield Center East, Chesterfield, MO
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $138 total per night from Sep 7 to Sep 8
$138 total
Sep 7 - Sep 8
Total includes taxes and fees
9.4/10 Exceptional! (1,001 reviews)
"Front desk staff was wonderful. Room was clean."
Reviewed on Aug 15, 2025
Hyatt Regency St. Louis at The Arch
315 Chestnut St, St. Louis, MO
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Aug 22 to Aug 23
$140 total
Aug 22 - Aug 23
Total includes taxes and fees
8.4/10 Very Good! (3,941 reviews)
"took 45 minutes to access main hotel in cae"
Reviewed on Aug 13, 2025
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.
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Hotels near Chesterfield Arts
- Hotels near Westfield Chesterfield Mall
- Hotels near Sophia M. Sachs Butterfly House
- Hotels near Faust Park
- Hotels near Sky Zone Indoor Trampoline Park - St. Louis
- Hotels near Chesterfield Sports Fusion
- Clarkson Valley Hotels
- Hotels near Myseum
- Hotels near Spirit of St. Louis
- Flights from Spirit of St. Louis
- Flights from Poplar Bluff (POF) to St. Louis (SUS)
- Flights from St. Louis (STL) to St. Louis (SUS)
- Flights from Mount Vernon (MVN) to St. Louis (SUS)
- Flights from Grand Rapids (GRR) to St. Louis (SUS)
- Flights from Los Angeles (LAX) to St. Louis (SUS)
- Flights from Joplin (JLN) to St. Louis (SUS)
- Flights from Atlanta (ATL) to St. Louis (SUS)
- Flights from Enid (WDG) to St. Louis (SUS)
- Flights from Minneapolis (MSP) to St. Louis (SUS)
- Flights from Detroit (DTW) to St. Louis (SUS)
- Flights from Las Vegas (LAS) to St. Louis (SUS)
- Flights from Lexington (LEX) to St. Louis (SUS)
- Flights from Chicago (ORD) to St. Louis (SUS)
- Flights from Kansas City (MCI) to St. Louis (SUS)
- Flights from Nashville (BNA) to St. Louis (SUS)
- Flights from Philadelphia (PHL) to St. Louis (SUS)
- Flights from Cincinnati (CVG) to St. Louis (SUS)
- Flights from Denver (DEN) to St. Louis (SUS)
- Flights from Evansville (EVV) to St. Louis (SUS)
- Flights from Raleigh (RDU) to St. Louis (SUS)
- Flights from Hagerstown (HGR) to St. Louis (SUS)
- Flights from Phoenix (PHX) to St. Louis (SUS)
- Flights from Cleveland (CLE) to St. Louis (SUS)
- Flights from Rock Sound (RSD) to St. Louis (SUS)
- Flights from Akron (CAK) to St. Louis (SUS)
- Flights from Norfolk (ORF) to St. Louis (SUS)
- Flights from Austin (AUS) to St. Louis (SUS)
- Flights from Orlando (MCO) to St. Louis (SUS)
- Flights from Dallas (DFW) to St. Louis (SUS)
- Flights from Topeka (FOE) to St. Louis (SUS)
- Flights from Milwaukee (MKE) to St. Louis (SUS)
- Flights from Tampa (TPA) to St. Louis (SUS)
- Flights from Springfield (SPI) to St. Louis (SUS)
- Flights from Fort Worth (FTW) to St. Louis (SUS)
- Flights from Memphis (MEM) to St. Louis (SUS)
- Flights from Boston (BOS) to St. Louis (SUS)
- Flights from Lawrenceville (LWV) to St. Louis (SUS)
- Flights from Savannah (SAV) to St. Louis (SUS)
- Flights from Columbus (CMH) to St. Louis (SUS)
- Flights from Jackson (JAN) to St. Louis (SUS)
- Flights from Colorado Springs (COS) to St. Louis (SUS)
- Flights from Richmond (RIC) to St. Louis (SUS)
- Flights from Orange County (SNA) to St. Louis (SUS)
- Flights from Fort Myers (RSW) to St. Louis (SUS)
- Flights from Miami (MIA) to St. Louis (SUS)
- Flights from Fort Dodge (FOD) to St. Louis (SUS)
- Flights from Knoxville (TYS) to St. Louis (SUS)
- Flights from Oakland (OAK) to St. Louis (SUS)
- Flights from Oklahoma City (OKC) to St. Louis (SUS)
- Flights from Leesburg (LEE) to St. Louis (SUS)
- Flights from Lafayette (LFT) to St. Louis (SUS)
- Flights from Manila (MNL) to St. Louis (SUS)
- Flights from Yangon (RGN) to St. Louis (SUS)
- Flights from Dallas (DAL) to St. Louis (SUS)
- Flights from Green Bay (GRB) to St. Louis (SUS)
- Flights from Fayetteville (XNA) to St. Louis (SUS)
- Flights from Huntsville (HSV) to St. Louis (SUS)
- Flights from San Angelo (SJT) to St. Louis (SUS)
- Flights from San Francisco (SFO) to St. Louis (SUS)
- Flights from Newton (EWK) to St. Louis (SUS)
- Flights from Vancouver (YVR) to St. Louis (SUS)
- Flights from Jacksonville (JAX) to St. Louis (SUS)
- Flights from Riga (RIX) to St. Louis (SUS)
- Flights from Montreal (YUL) to St. Louis (SUS)
- Flights from Fukushima (FKS) to St. Louis (SUS)
- Flights from Fresno (FAT) to St. Louis (SUS)
- Flights from Toronto (YYZ) to St. Louis (SUS)
- Flights from San Diego (SAN) to St. Louis (SUS)
- Flights from New York (LGA) to St. Louis (SUS)
- Flights from Matamoros (MAM) to St. Louis (SUS)
- Flights from Trenton (TTN) to St. Louis (SUS)
- Flights from Jonesboro (JBR) to St. Louis (SUS)
- Car rentals near Sky Zone Indoor Trampoline Park - St. Louis
- Car rentals near Clarkson Valley
- Car rental St. Louis Airport (SUS)
- Enterprise Rental Cars in Spirit of St. Louis
- Budget Rental Cars in Spirit of St. Louis
- Avis Rental Cars in Spirit of St. Louis
- Hertz Rental Cars in Spirit of St. Louis
- National Car Rental Rental Cars in Spirit of St. Louis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.