Chesterfield Vacations from $240
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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.
Hilton Garden Inn Chesterfield
Price was $334, price is now $240 per person
$240
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (767 reviews)
Just a really nice hotel tucked away from everything, but still close to get whereevre you need to go!
Reviewed on Oct 26, 2025
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
Grand Center
Price was $389, price is now $283 per person
$283
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,013 reviews)
My stay here was truly awesome! No complaints AT ALL! The front desk receptionist Dillion went out of his way to ensure my stay was smooth and peaceful as possible. I will be back!
Reviewed on Nov 10, 2025
The Cheshire
Price was $404, price is now $300 per person
$300
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,008 reviews)
Our room was very nice. The staff were always willing to be helpful. Breakfast was amazing! With the added perk of Starbucks in a cosy, quaint coffeeshop as part of the Cheshire.
Our stay was perfect.
Reviewed on Nov 4, 2025
Don't see what you're looking for?
See all available trips from Oskaloosa to Chesterfield
View all tripsDiscover the most popular places to visit in Chesterfield
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 great live music or attend a baseball game.
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.
St. Louis Zoo
4.5/5(1,212 reviews)
In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.
What to do in Chesterfield
St Louis: City Museum General Admission Ticket
$22
per adult
96% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
$26
per adult
Lemp Haunted Neighborhood Walking Tour
$27
per adult
84% of travellers recommend
Chesterfield Hotel Deals
Hyatt Place St. Louis/Chesterfield
333 Chesterfield Center East, Chesterfield, MO
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $143 total per night from Nov 23 to Nov 24
$143 total
Nov 23 - Nov 24
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
Very nice and clean hotel. Staff were excellent. Would definitely recommend. The only criticism I would make is that the complementary coffee offered is awful.
Reviewed on Nov 3, 2025
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 Nov 18 to Nov 19
$108 total
Nov 18 - Nov 19
Total with taxes and fees
7.8/10 Good! (1,015 reviews)
Everything was great!! We loved having apartment like rooms!! Very dog friendly!
Reviewed on Nov 3, 2025
Drury Plaza Hotel St. Louis Chesterfield
355 Chesterfield Ctr, Chesterfield, MO
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $151 total per night from Nov 16 to Nov 17
$151 total
Nov 16 - Nov 17
Total with taxes and fees
9.6/10 Exceptional! (1,017 reviews)
Good breakfast and great to have coffee and soft drinks available. Having the "kickback" was especially helpful
Reviewed on Nov 5, 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.
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
