Chesterfield Vacation Packages

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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.

Top Chesterfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
per person
Aug 8 - Aug 11
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
9/10 Wonderful! (1,547 reviews)
TV worked half the time. Hardly any hot water.

Reviewed on Jun. 28, 2025

Hilton St. Louis at the Ballpark

Hilton St. Louis at the Ballpark

4 out of 5
Downtown St. Louis
per person
Aug 8 - Aug 11
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
7.6/10 Good! (1,008 reviews)
This was my 3rd time staying at this property. This was the first time I had any complaints, the air in the room wasn’t cooling at all, the water pressure in the shower was horrible unless you had it all the way on hot. Bathroom floor was very first, toilet hardly flushed. Otherwise, everything was great!

Reviewed on Jun. 27, 2025

DoubleTree by Hilton St. Louis Forest Park

DoubleTree by Hilton St. Louis Forest Park

4 out of 5
Central West End
per person
Aug 8 - Aug 11
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.2/10 Very Good! (1,003 reviews)
Stay here a lot for my spouses visits to BJH. So easy for hospital stays, AppleBees is great to have and is attached to hotel. Always nice, clean and comfortable.

Reviewed on Jun. 24, 2025

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
per person
Aug 8 - Aug 11
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
9/10 Wonderful! (1,759 reviews)
I love staying at the moonrise hotel Love the rooftop especially at night

Reviewed on Jun. 26, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
Aug 8 - Aug 11
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.4/10 Very Good! (1,000 reviews)
Room had issues. Addressed with staff.

Reviewed on Jun. 25, 2025

Ready to book your vacation to Chesterfield?

 

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Chesterfield Hotel Deals

Sonesta ES Suites St. Louis - Chesterfield
Sonesta ES Suites St. Louis - Chesterfield
3 out of 5
15431 Conway Rd, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jul 29 to Jul 30
CA $147
CA $170 total
Jul 29 - Jul 30
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"I liked having a 2 bedroom suite with 2 bathrooms. The kitchen area was good but no coffee in the suite."

Reviewed on Jun. 26, 2025

Sonesta ES Suites St. Louis - Chesterfield
Hyatt Place St. Louis/Chesterfield
Hyatt Place St. Louis/Chesterfield
3 out of 5
333 Chesterfield Center East, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jul 6 to Jul 7
CA $174
CA $202 total
Jul 6 - Jul 7
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Long weekend in St Louis/Chesterfield
"Our stay was wonderful. We were in town to celebrate a family members accomplishments that lives nearby. We picked the perfect place. Great, newer, clean comfortable hotel. Friendly staff, indoor pool, fitness center, free breakfast, free covered underground parking, great location near shopping, ..."

Reviewed on Jun. 26, 2025

Hyatt Place 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
The price is CA $177 per night from Jun 30 to Jul 1
CA $177
CA $208 total
Jun 30 - Jul 1
includes taxes & fees
8.4/10 Very Good! (3,792 reviews)
"Very clean"

Reviewed on Jun. 27, 2025

Hyatt Regency St. Louis at The Arch
See all 2,076 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from CA $880 on Expedia, you'll be pleasantly surprised at how much a vacation to Chesterfield costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chesterfield?
You can typically find lower prices and better availability in December, January and February. Take a look at our cheap Chesterfield vacation packages and you could land some great off-season discounts.
How many days is enough for Chesterfield?
Chesterfield vacations can be as short or long as you like, but to get a real feel for this destination, we'd suggest 2 days is a good ballpark. This will mean you can visit major attractions like The Factory and Chesterfield Sports Fusion as well as lesser-known spots. Don't forget to explore cool areas such as Clarkson Valley and Winchester either. If you're clever with your time, you can even schedule a day trip outside of Chesterfield too.
Is it worth booking a vacation package to Chesterfield?
Chesterfield has all the ingredients you need for an amazing break --- golfing, nature and shopping are just the start. Whether you want to check out sights such as The Factory and Chesterfield Sports Fusion, or venture off the beaten track, you'll find plenty to see and do on your Chesterfield vacation.
How to find the best Chesterfield package deals?
Start your search for a Chesterfield package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Chesterfield package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chesterfield getaway off to a flying start.
Is it cheaper to book a Chesterfield vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can customize your Chesterfield trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chesterfield?
If you're considering a spur-of-the-moment Chesterfield trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Chesterfield?

  1. Choose your dates: The things you plan to do in Chesterfield and your favourite season can help you decide when to go.
  2. Set a budget: Factor in expenses such as flights, food and transportation when calculating how much to save for your trip to Chesterfield. Then, pick a property that fits your budget, whether that's a low-cost option or a more upscale retreat.
  3. Decide how long to go for: Now that you know more about Chesterfield, you can figure out the ideal length of your vacation. Put together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, lock in the right Chesterfield vacation package for you.

Discover the most popular places to visit in Chesterfield

Busch Stadium

Busch Stadium

5/5(19 reviews)

Busch Stadium is one of the more well-known attractions to visit during your trip to St. Louis. Experience the area's acclaimed art scene or attend a baseball game.

Busch Stadium
St. Louis Zoo

St. Louis Zoo

4.5/5(7 reviews)

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

St. Louis Zoo
Gateway Arch featuring modern architecture, a city and a skyscraper

Gateway Arch

4.5/5(37 reviews)

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch

What to do in Chesterfield

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

CA $31
per adult
94% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

CA $33
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
St Louis Self-Guided Driving and Walking Audio Tour

St Louis Self-Guided Driving and Walking Audio Tour

CA $23
per traveller
St Louis Self-Guided Driving and Walking Audio Tour
See all activities in Chesterfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.