Chesterfield Vacations from $218

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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.
Hampton Inn St. Charles St. Peters

Hampton Inn St. Charles St. Peters

2.5 out of 5
Save 100% on your flight
Price was $299, price is now $218 per person
$218
per person
Sep 17 - Sep 20
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8/10 Very Good! (1,004 reviews)
This hotel has just been upgraded the staff was amazing the breakfast was terrific with plenty of selections and the hotel is very well maintained and meticulously taken care of.

Reviewed on Jul 13, 2026

Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Price was $702, price is now $367 per person
$367
per person
Sep 3 - Sep 7
found 15 hours 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

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Save 100% on your flight
Price was $341, price is now $228 per person
$228
per person
Sep 17 - Sep 20
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.4/10 Very Good! (831 reviews)
Very clean and very nice as a little home away from home. It’s just up the road from shops and all kinds of restaurants. When I make another trip back up there this will be my first choice again!!

Reviewed on Jul 7, 2026

White House at Grand Central

White House at Grand Central

3.5 out of 5
Grand Center
Save 100% on your flight
Price was $339, price is now $243 per person
$243
per person
Sep 11 - Sep 13
found 1 day 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

Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $408, price is now $294 per person
$294
per person
Sep 17 - Sep 20
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,096 reviews)
I booked a room with 2 queen beds well in advance of the reservation date. When we arrived I was given a kind bed and a roll away. This was a special weekend for 2 guys traveling to see baseball games for an entire weekend.

Reviewed on Jul 15, 2026

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Stay near popular Chesterfield attractions

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.
See properties

What to do in Chesterfield

The Gateway Arch National Park & Museum

StL's Signature "Sights and Bites" - Private Tour in St. Louis

$165
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

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

Lemp Haunted Neighborhood Walking Tour

$25
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Chesterfield

Chesterfield Hotel Deals

Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

3 out of 5
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $151 total per night from Jul 26 to Jul 27
$151 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (1,204 reviews)
"Great staff, room was very clean. Amazing breakfast and happy hour with food."

Reviewed on Jul 13, 2026

Drury Plaza Hotel St. Louis Chesterfield
Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4 out of 5
315 Chestnut St St. Louis MO
$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! (4,107 reviews)
"We had no air in our room called, they came and checked on it couldn't get it to stay. They had no other rooms available they did bring us fans but it was still bad. They offered no money back. They did offer us breakfast but I feel like that was already free... April Enlow"

Reviewed on Jul 14, 2026

Hyatt Regency St. Louis at The Arch
Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

3.5 out of 5
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $111 total per night from Aug 9 to Aug 10
$111 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (3,246 reviews)
"The front desk staff was friendly and helpful, especially Desire who was engaging, kind and took the time to help me with all my questions. Breakfast was delicious and had a great variety of hot and cold foods. Parking was easy to get in/out and free as long as you validated your ticket at the front ..."

Reviewed on Jul 14, 2026

Clayton Plaza Hotel & Extended Stay
See all 2,290 properties in Chesterfield
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 $218 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?

  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 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 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.