
Chesterfield Vacations from $243
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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.

White House at Grand Central
Grand Center
Save 100% on your flight
Price was $339, price is now $243 per person
$243
per person
Sep 11 - Sep 13
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.4/10 Very Good! (144 reviews)
We liked the location of this hotel—it's right on campus or just across the street, making it feel safe and convenient. You’re only a couple of blocks away from fast food, Walgreens, and the bus, which was so convenient. The area feels regal and historic with beautifully manicured lawns, and everything was just as pictured. The air conditioning worked well, all the amenities were in place, and we really enjoyed the old-timey charm.
The only minor suggestion I have is about the check-in process. Instead of having to haul luggage to a sister hotel to provide a credit card, it would be great to handle that by phone. It would save that extra trip, especially in the heat. Otherwise, it was a wonderful stay!
Reviewed on Jun 29, 2026

The Wildwood Hotel
Price was $558, price is now $278 per person
$278
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,661 reviews)
We enjoyed our stay. Very helpful staff. Clean all the way around. Nice sized room and bathroom. Nice surrounding area. Convenient parking in the attached ramp (forget the on street parking.)
Reviewed on Jul 14, 2026

Remodeled and Inviting Free EV
Save 100% on your flight
Price was $571, price is now $316 per person
$316
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
10/10 Exceptional! (1 review)
The property was excellent, and the home was very warm and welcoming.
Reviewed on Jun 25, 2026

The Cheshire
Save 100% on your flight
Price was $517, price is now $364 per person
$364
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
The room was fine but I had to request a mini fridge which surprised me. They seem to be standard in most hotel rooms these days. The front desk staff did what we asked but looked at us like we were bothering them. There was one person in particular who sat behind the desk either on her phone or crocheting. When I asked if someone could refill the ice water that was in the lobby (it was a very hot day) she looked at me and said, "you can buy a bottle of water." Not long after, the water was refilled. There was one nice gentleman who clearly worked there (not at the desk) who handed us an umbrella during a storm as we were trying to go out to dinner. On our last day we asked the front desk for a late check-out. There was different staff and they said we could check out at noon (and were very pleasant about it). Unfortunately, they failed to notify the cleaning staff and they were banging on our door all morning. One person walked in as we were getting dressed. She was very apologetic and told us that they were not told taht we had late checkout. I would definitely not stay there again.
Reviewed on Jul 14, 2026

Hermann Grain Bins BNB
Save 100% on your flight
Price was $1,837, price is now $1,356 per person
$1,356
per person
Sep 17 - Sep 23
found 23 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
6/10 (2 reviews)
It was so comfortable and uniquely and beautifully decorated! There was so many awesome areas to explore inside and outside of the Grain Bins. Food provided for breakfast was fresh and hot. There was perfectly cooked bacon, scrambled eggs and really moist corn muffins with homemade mango preservers! We were welcomed with fresh, homemade plum bread. Instructions for everything available to utilize and operate were easy to understand. I can’t wait to go back and I will tell all my friends and family about this unique and relaxing place.
Reviewed on May 22, 2026
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What to do in Chesterfield

StL's Signature "Sights and Bites" - Private Tour in St. Louis
$165
per adult

St. Louis Ghost Tour: Sinister Sins & Shadows
$24
per adult
100% of travellers recommend

St. Louis Premium Small Group Tour With Arch & River Cruise
$169
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
$136 nightly
The price is $158 total per night from Jul 19 to Jul 20
$158 total
Jul 19 - Jul 20
Total with taxes and fees
9.6/10 Exceptional! (1,220 reviews)
"Great staff, room was very clean. Amazing breakfast and happy hour with food."
Reviewed on Jul 13, 2026

Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $158 total per night from Jul 19 to Jul 20
$158 total
Jul 19 - Jul 20
Total with taxes and fees
8.6/10 Excellent! (4,248 reviews)
"."
Reviewed on Jul 14, 2026

Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $110 total per night from Aug 9 to Aug 10
$110 total
Aug 9 - Aug 10
Total with taxes and fees
8.8/10 Excellent! (3,302 reviews)
"Room was very spacious, shower was awesome, everything was nice and clean. Pool was open and looked nice, did not have the breakfast although it smelled good. Great dining options were within walking distance, neighborhood felt very safe. Young lady at front desk was very friendly and helpful with ..."
Reviewed on Jul 14, 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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- 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.



















