Title: Chesterfield Vacation Packages 2026 from $662 | Expedia.com [Chesterfield Travel Guide](https://expedia.com/Chesterfield.dx9530)[Hotels in Chesterfield](https://expedia.com/Chesterfield-Hotels.d9530.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.com/Chesterfield-Vacation-Rentals.d9530.Travel-Guide-VacationRentals)[Flights to Chesterfield](https://expedia.com/Cheap-Flights-To-Chesterfield.d9530.Travel-Guide-Flights)[Things to do in Chesterfield](https://expedia.com/Things-To-Do-In-Chesterfield.d9530.Travel-Guide-Activities)[Car Rentals in Chesterfield](https://expedia.com/Car-Rentals-In-Chesterfield.d9530.Car-Rental-Guide) ![](https://images.trvl-media.com/place/9530/71d53939-4b56-4c98-803c-432ac6ed1c41.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesterfield Vacations from $662 ## Book a Hotel + Flight or Car together to unlock savings - ## 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](https://www.expedia.com/St-Louis-Premium-Outlets-St-Louis.d553248621561876860.Vacation-Attraction), [Lou Fusz Soccer Complex](https://www.expedia.com/Lou-Fusz-Soccer-Complex-St-Louis.d553248635975913244.Vacation-Attraction) and [Westfield Chesterfield Mall](https://www.expedia.com/Westfield-Chesterfield-Mall-St-Louis.d6190516.Vacation-Attraction) 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. ![The Wildwood Hotel](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/035dee6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wildwood Hotel $662 per person May 13 - May 16 found 1 day ago Roundtrip flight included New York (JFK) to St. Louis (STL) 9.2/10 Wonderful! (1,627 reviews) The breakfaat was average, thou fresh. There was enough street parking nearby, safe. Reviewed on Mar 30, 2026 ![Marriott St. Louis West](https://images.trvl-media.com/lodging/1000000/20000/17400/17345/cec6cc0f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott St. Louis West $784 per person May 17 - May 23 found 13 hours ago Roundtrip non-stop flight included Los Angeles (LAX) to St. Louis (STL) 8.4/10 Very Good! (1,003 reviews) Overall property was in great location and staff was good-especially wait staff at bar and restaurant. Concierge amenities closed on weekends so please be aware when booking this. The water smelled of sulfur when coming out of faucet. Reviewed on Mar 9, 2026 ![The Mercantile on the Katy Trail](https://images.trvl-media.com/lodging/104000000/103390000/103386000/103385931/2e86baed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Mercantile on the Katy Trail $871 per person May 12 - May 17 found 11 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to St. Louis (STL) 9.8/10 Exceptional! (29 reviews) Very nice. Fully equipped with everything you need and more! The extras really added to the overall experience. Clean, quiet, and safe. Comfortable. Great communication. I definitely recommend staying here if you are in the area! Reviewed on Nov 8, 2025 ![Up Up and Away Lodging](https://images.trvl-media.com/lodging/31000000/30550000/30549000/30548920/b719c569_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Up Up and Away Lodging $1,100 per person May 12 - May 17 found 11 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to St. Louis (STL) 9.4/10 Exceptional! (27 reviews) Yes! The room was beautiful. Very clean. Beth was an amazing hostess, and the breakfast hit the spot. I highly recommend the stay, and when I return, I will do the same B&B. Thanks, Beth! Reviewed on Dec 5, 2025 ![The Cheshire](https://images.trvl-media.com/lodging/1000000/30000/26100/26061/24983857_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Cheshire $937 per person May 13 - May 16 found 1 day ago Roundtrip flight included New York (JFK) to St. Louis (STL) 8.6/10 Excellent! (1,009 reviews) It had unique decor which was fun. Staff was nice But the lights were broken and there was a leftover can under a chair Reviewed on Apr 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Chesterfield [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-07/2026-05-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=STL&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Chesterfield ![Union Station, St. Louis, MO](https://images.trvl-media.com/place/502868/8704491b-9324-4c56-89ed-94a638702313.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/St-Louis-Union-Station-Downtown-West.d502868.Vacation-Attraction) ![Busch Stadium](https://images.trvl-media.com/place/3284/67189e41-0060-455b-85a9-ab65c9125a63.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Busch-Stadium-Downtown-St-Louis.d502872.Vacation-Attraction) ![Gateway Arch](https://images.trvl-media.com/place/502855/34e3411a-eeba-4fa1-95fe-3ad9b54938f4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Gateway Arch Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark. [](https://expedia.com/Gateway-Arch-Downtown-St-Louis.d502855.Vacation-Attraction) ### What to do in Chesterfield ![St. Louis: Gateway Ghouls and Hauntings Walking Tour](https://mediaim.expedia.com/localexpert/47668485/dd78fc5b-2837-423e-80a2-c4dfd8151a08.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### St. Louis Ghost Tour: Sinister Sins & Shadows $24 per adult [](https://expedia.com/things-to-do/st-louis-ghost-tour-sinister-sins-shadows.a47668485.activity-details) ![Lemp Haunted Neighborhood Walking Tour](https://mediaim.expedia.com/localexpert/1357747/5cac0135-b8b0-4916-b5c1-48e8a0a93aab.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Lemp Haunted Neighborhood Walking Tour $30 per adult **84%** of travellers recommend [](https://expedia.com/things-to-do/lemp-haunted-neighborhood-walking-tour.a1357747.activity-details) ![St. Louis Premium Driving Tour with Boat Ride & Arch](https://mediaim.expedia.com/localexpert/47712556/5e48de69-a78b-4315-bccd-6ae9dafd98a3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### St. Louis Premium Driving Tour with Boat Ride & Arch $174 per adult **100%** of travellers recommend [](https://expedia.com/things-to-do/st-louis-premium-driving-tour-with-boat-ride-arch.a47712556.activity-details) [See all activities in Chesterfield](https://expedia.com/things-to-do/search?rid=9530) ## Chesterfield Hotel Deals ![Drury Plaza Hotel St. Louis Chesterfield](https://images.trvl-media.com/lodging/2000000/1350000/1346800/1346760/69d580ec_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Drury Plaza Hotel St. Louis Chesterfield 355 Chesterfield Ctr Chesterfield MO Fully refundableReserve now, pay when you stay $136 nightly $158 total Apr 12 - Apr 13 Total with taxes and fees 9.6/10 Exceptional! (1,132 reviews) Staff was very friendly and helpful. Property was well maintained and clean with plenty of amenities above regular hotel standard at an affordable price. Reviewed on Apr 7, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=1346760&PinnedHotelID=1346760&HadPinnedHotel=true®ionId=9530) ![Sonesta ES Suites St. Louis - Chesterfield](https://images.trvl-media.com/lodging/1000000/10000/500/422/6f160867_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta ES Suites St. Louis - Chesterfield 15431 Conway Rd Chesterfield MO Fully refundableReserve now, pay when you stay $104 nightly $121 total Apr 8 - Apr 9 Total with taxes and fees 8/10 Very Good! (1,026 reviews) Property is very run down. Both toilets didn’t stop running. One all night long and one off and on all night long. The stair carpet is beyond gross and looks like it’s never been clean. Paint and caulk touch ups were attempted it appeared, but def looked rushed/cheaply done. Needs some major updates ... Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F8%2F2026&endDate=4%2F9%2F2026&selected=422&PinnedHotelID=422&HadPinnedHotel=true®ionId=9530) ![Hyatt Place St. Louis/Chesterfield](https://images.trvl-media.com/lodging/7000000/6590000/6583800/6583788/8b8909bb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place St. Louis/Chesterfield 333 Chesterfield Center East Chesterfield MO Fully refundableReserve now, pay when you stay $130 nightly $150 total Apr 19 - Apr 20 Total with taxes and fees 9.6/10 Exceptional! (1,004 reviews) Everything was great. It did seem like the one gentleman was just doing enough to get through the day. Not angry but no cheer or warm greeting at all. Karen was very happy which was nice. Bed was comfy room was clean bathroom was clean. Food was alright. I got chicken wings and the Parmesan fries. ... Reviewed on Apr 6, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=6583788&PinnedHotelID=6583788&HadPinnedHotel=true®ionId=9530) [See all 2,211 properties in Chesterfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F8%2F2026&endDate=4%2F9%2F2026®ionId=9530) 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](https://www.expedia.com/Six-Flags-St-Louis-St-Louis.d6147083.Vacation-Attraction), [Magic House - St. Louis Childrens Museum](https://www.expedia.com/Magic-House-St-Louis-Childrens-Museum-St-Louis.d6191631.Vacation-Attraction) and [Route 66 State Park](https://www.expedia.com/Route-66-State-Park-St-Louis.d6292976.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) 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[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Chesterfield vacation package cost? ### What are the cheapest months to go to Chesterfield? ### How many days is enough for Chesterfield? ### Is it worth booking a vacation package to Chesterfield? ### How to find the best Chesterfield package deals? ### Is it cheaper to book a Chesterfield vacation as a package? ### When to book a vacation package to Chesterfield? ### 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](https://www.expedia.com/why/trip-planning) 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](https://www.expedia.com/Things-To-Do-In-Chesterfield.d9530.Travel-Guide-Activities) 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? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Chesterfield Arts ](https://www.expedia.com/Chesterfield-Arts-Hotels.0-l553248621532648594-0.Travel-Guide-Filter-Hotels) - [Hotels near Westfield Chesterfield Mall ](https://www.expedia.com/Westfield-Chesterfield-Mall-Hotels.0-l6190516-0.Travel-Guide-Filter-Hotels) - [Hotels near Sophia M. 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[Flights from Montreal (YUL) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/yul/sus/montreal-to-st-louis) - [Flights from Fukushima (FKS) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/fks/sus/fukushima-to-st-louis) - [Flights from Fresno (FAT) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/fat/sus/fresno-to-st-louis) - [Flights from Toronto (YYZ) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/yyz/sus/toronto-to-st-louis) - [Flights from San Diego (SAN) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/san/sus/san-diego-to-st-louis) - [Flights from New York (LGA) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/lga/sus/new-york-to-st-louis) - [Flights from Matamoros (MAM) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/mam/sus/matamoros-to-st-louis) - [Flights from Trenton (TTN) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/ttn/sus/trenton-to-st-louis) - [Flights from Jonesboro (JBR) to St. Louis (SUS) ](https://www.expedia.com/lp/flights/jbr/sus/jonesboro-to-st-louis) - [Chesterfield Arts ](https://www.expedia.com/Chesterfield-Arts-St-Louis.d553248621532648594.Vacation-Attraction) - [Westfield Chesterfield Mall ](https://www.expedia.com/Westfield-Chesterfield-Mall-St-Louis.d6190516.Vacation-Attraction) - [Sophia M. Sachs Butterfly House ](https://www.expedia.com/Sophia-M-Sachs-Butterfly-House-St-Louis.d6190513.Vacation-Attraction) - [Faust Park ](https://www.expedia.com/Faust-Park-St-Louis.d6160334.Vacation-Attraction) - [Taubman Prestige Outlets ](https://www.expedia.com/Taubman-Prestige-Outlets-St-Louis.d553248621561876633.Vacation-Attraction) - [Sky Zone Indoor Trampoline Park - St. Louis ](https://www.expedia.com/Sky-Zone-Indoor-Trampoline-Park-St-Louis-St-Louis.d553248621532648592.Vacation-Attraction) - [Chesterfield Sports Fusion ](https://www.expedia.com/Chesterfield-Sports-Fusion-St-Louis.d553248621532648590.Vacation-Attraction) - [Myseum ](https://www.expedia.com/Myseum-St-Louis.d6292383.Vacation-Attraction) - [Lou Fusz Soccer Complex ](https://www.expedia.com/Lou-Fusz-Soccer-Complex-St-Louis.d553248635975913244.Vacation-Attraction) - [Ballwin Vacations ](https://www.expedia.com/Ballwin.d6354554.Destination-Travel-Guides) - [Car rentals near Sky Zone Indoor Trampoline Park - St. Louis ](https://www.expedia.com/Car-Rentals-In-Sky-Zone-Indoor-Trampoline-Park-St-Louis.d553248621532648592.Car-Rental-Guide) - [Car rentals near Clarkson Valley ](https://www.expedia.com/Car-Rentals-In-Clarkson-Valley.d553248634983528759.Car-Rental-Guide) - [Car rental St. Louis Airport (SUS) ](https://www.expedia.com/Car-Rentals-In-Spirit-Of-St-Louis.d6024951.Car-Rental-Guide) - [Enterprise Rental Cars in Spirit of St. Louis ](https://www.expedia.com/Enterprise-Car-Rentals-In-Spirit-Of-St-Louis.d6024951-c15.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Spirit of St. Louis ](https://www.expedia.com/Budget-Car-Rentals-In-Spirit-Of-St-Louis.d6024951-c39.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Spirit of St. Louis ](https://www.expedia.com/Avis-Car-Rentals-In-Spirit-Of-St-Louis.d6024951-c41.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Spirit of St. Louis ](https://www.expedia.com/Hertz-Car-Rentals-In-Spirit-Of-St-Louis.d6024951-c40.Car-Rental-Guide-Suppliers) - [National Car Rental Rental Cars in Spirit of St. Louis ](https://www.expedia.com/National-Car-Rental-Car-Rentals-In-Spirit-Of-St-Louis.d6024951-c42.Car-Rental-Guide-Suppliers) \* Savings based on package bookings compared to the price of the same components booked separately. 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