Chesterfield Vacations from $696

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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.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,232, price is now $696 per person
$696
per person
Aug 4 - Aug 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
9.2/10 Wonderful! (1,663 reviews)
We were welcomed by a lovely person named Genna at the front desk who was so kind. The room was great - very clean and spacious. The grounds and building seem very well taken care of. This was a blind find on our way through the area. We sure lucked out with such a fantastic stay!

Reviewed on Jun 29, 2026

The Cheshire

The Cheshire

4 out of 5
Price was $1,130, price is now $824 per person
$824
per person
Aug 4 - Aug 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
8.8/10 Excellent! (1,000 reviews)
I appreciated the open coffee bar and snacks.

Reviewed on Jun 29, 2026

Landing Amazing 1bd, Yoga Studio, Gym

Landing Amazing 1bd, Yoga Studio, Gym

3 out of 5
DeBaliviere Place
Price was $1,317, price is now $1,021 per person
$1,021
per person
Aug 4 - Aug 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
No reviews
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was $885, price is now $698 per person
$698
per person
Aug 4 - Aug 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
8.4/10 Very Good! (830 reviews)
Good all around place to stay nothing exceptional or wowing

Reviewed on Jun 19, 2026

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was $897, price is now $710 per person
$710
per person
Aug 4 - Aug 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
8.8/10 Excellent! (1,074 reviews)
Should have earlier check in

Reviewed on Jun 29, 2026

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Stay near popular Chesterfield attractions

St. Louis Premium Outlets

8.8/5 (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

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
Best of St. Louis Small Group Tour w/ Arch & River Cruise

St. Louis Premium Small Group Tour With Arch & River Cruise

$161
per adult
84% of travellers recommend
St. Louis Premium Small Group Tour With Arch & River Cruise
St. Louis Premium Driving Tour with Boat Ride & Arch

St. Louis Premium Driving Tour with Boat Ride & Arch

$174
per adult
100% of travellers recommend
St. Louis Premium Driving Tour with Boat Ride & Arch
See all activities in Chesterfield

Chesterfield Hotel Deals

Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

3 out of 5
15431 Conway Rd Chesterfield MO
$101 nightly
The price is $117 total per night from Jul 7 to Jul 8
$117 total
Jul 7 - Jul 8
Total with taxes and fees
8/10 Very Good! (1,040 reviews)
"The only reason(s) im not leaving a 5 star review is because the walls & windows are super thin that you can easily hear the birds & the cars & if youre even 2 buildings from the pool, you can hear all the excitement from everyone. Im a light sleeper, so that may not be anyone else's concern. The ..."

Reviewed on Jun 29, 2026

Sonesta ES Suites St. Louis - Chesterfield
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 5 to Jul 6
$151 total
Jul 5 - Jul 6
Total with taxes and fees
9.6/10 Exceptional! (1,202 reviews)
"."

Reviewed on Jun 29, 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
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $175 total per night from Jul 17 to Jul 18
$175 total
Jul 17 - Jul 18
Total with taxes and fees
8.6/10 Excellent! (4,179 reviews)
"The property was in an excellent location to see many tourists areas. From the valet staff to the bell staff to the check in staff everyone was extremely courteous, helpful and went out of their way to do everything for you. The entire property was well maintained and clean. Our room was clean, well ..."

Reviewed on Jun 30, 2026

Hyatt Regency St. Louis at The Arch
See all 2,260 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 $696 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.