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.
Holiday Inn Express & Suites St. Louis West - Fenton by IHG

Holiday Inn Express & Suites St. Louis West - Fenton by IHG

3 out of 5
per person
Nov 2 - Nov 4
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
great hotel clean and staff was fantasic

Reviewed on Aug. 3, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
per person
Sep 13 - Sep 15
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
9.2/10 Wonderful! (1,558 reviews)
Great place to stay.

Reviewed on Aug. 12, 2025

Comfort Suites Rolla

Comfort Suites Rolla

2.5 out of 5
per person
Sep 15 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (872 reviews)
The breakfast was pretty good. Served biscuits/gravy (and the biscuits were NOT rock hard like most hotel breakfasts), bacon, eggs, muffins, and waffles. Breakfast was included. Room was clean. Overall, good stay.

Reviewed on Aug. 2, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Sep 13 - Sep 15
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.2/10 Very Good! (760 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul. 26, 2025

White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
per person
Oct 10 - Oct 13
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.6/10 Excellent! (114 reviews)
It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay.

Reviewed on Jul. 9, 2025

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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 $128 per night from Aug 20 to Aug 21
CA $128
CA $148 total
Aug 20 - Aug 21
includes taxes & fees
7.8/10 Good! (1,005 reviews)
Great suite
"2 bedroom condo with full kitchen was perfect for a family gathering"

Reviewed on Aug. 9, 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 $164 per night from Sep 7 to Sep 8
CA $164
CA $190 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
"Good stay!"

Reviewed on Aug. 10, 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
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Aug 22 to Aug 23
CA $164
CA $193 total
Aug 22 - Aug 23
includes taxes & fees
8.4/10 Very Good! (3,942 reviews)
"Good services and the staffs are friendly. I love it"

Reviewed on Aug. 10, 2025

Hyatt Regency St. Louis at The Arch
See all 2,056 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

Discover the most popular places to visit in Chesterfield

Busch Stadium

Busch Stadium

5/5(19 reviews)

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.

Busch Stadium
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
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

What to do in Chesterfield

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

CA $31
per adult
96% 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
Best of St. Louis Small Group Tour w/ Arch & River Cruise

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

CA $232
per adult
84% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from CA $776 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.

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