Chesterfield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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
Price was CA $1,007, price is now CA $725 per person
CA $725
per person
Oct 11 - Oct 14
found 8 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to St. Louis (STL)
9.2/10 Wonderful! (1,661 reviews)

The Cheshire

The Cheshire

4 out of 5
Price was CA $1,330, price is now CA $1,078 per person
CA $1,078
per person
Oct 9 - Oct 12
found 12 hours ago
Roundtrip flight included
Halifax (YHZ) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
Pretty location. Direct access to the park. Cycled everywhere. Private secure car park.

Reviewed on Jul 15, 2026

Landing Furnished Apartments - Central West End

Landing Furnished Apartments - Central West End

3.5 out of 5
Central West End
Price was CA $1,660, price is now CA $1,479 per person
CA $1,479
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
7/10 Good! (4 reviews)
Parking was behind a large mechanical gate which did not always work. Could sometimes be noisy outside in the evening due to college clientele. Had to park on the street most of the time because of gate issues.

Reviewed on Jul 6, 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $1,122, price is now CA $1,023 per person
CA $1,023
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Everything was great, just wish the kids had pool access.

Reviewed on Jul 15, 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 CA $1,338, price is now CA $1,224 per person
CA $1,224
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.8/10 Excellent! (1,061 reviews)

Ready to book your vacation to Chesterfield?

 

Choose your dates

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
The price is CA $183 per night from Aug 3 to Aug 4
CA $183
CA $212 total
Aug 3 - Aug 4
includes taxes & fees
9.6/10 Exceptional! (1,205 reviews)
"Good stay, however, room was the smallest two room suite I’ve ever had at a Drury and was an odd set up."

Reviewed on Jul 16, 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
The price is CA $188 per night from Jul 19 to Jul 20
CA $188
CA $222 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (4,110 reviews)
"The hotel was amazing! I went for 4th of July celebration. The downtown was crazy and crowded. The hotel staff was very helpful about events happening locally."

Reviewed on Jul 16, 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
The price is CA $136 per night from Aug 9 to Aug 10
CA $136
CA $159 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (3,250 reviews)
"Great location for the things we visited (City Foundry, Grant's Farm, Zoo, Cardinals game). Hotel was clean, beds were comfortable, bathrooms were updated. Breakfast was excellent - Tom makes the BEST omelettes."

Reviewed on Jul 16, 2026

Clayton Plaza Hotel & Extended Stay
See all 2,295 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

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

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

CA $34
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
The Gateway Arch National Park & Museum

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

CA $234
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

CA $36
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from CA $725 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.

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.