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.
Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
Price was CA $1,389, price is now CA $1,150 per person
CA $1,150
per person
Sep 30 - Oct 5
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.8/10 Excellent! (1,096 reviews)
Clean room

Reviewed on Jul 9, 2026

The Mercantile on the Katy Trail

The Mercantile on the Katy Trail

4.5 out of 5
Price was CA $1,811, price is now CA $1,424 per person
CA $1,424
per person
Sep 30 - Oct 5
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9.8/10 Exceptional! (34 reviews)
This was a really unique stay in a renovated building! Loved the modern amenities and charming decor. We were able to bring our English bulldog and enjoy many of the comforts of home. We will definitely stay again!

Reviewed on Jun 28, 2026

The Royal Sonesta Chase Park Plaza St. Louis

The Royal Sonesta Chase Park Plaza St. Louis

4.5 out of 5
Central West End
Price was CA $2,091, price is now CA $1,667 per person
CA $1,667
per person
Sep 30 - Oct 5
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9/10 Wonderful! (1,011 reviews)
Beautiful, clean, great pool. Parking is obnoxious and costly. All tech is outdated and slow, internet stinks. Lots of extra fees on absolutely everything for no reason, nickel and dime every detail. Locations was great for walking to lots of things, and all in-house dining was delicious!

Reviewed on Jul 9, 2026

21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
Downtown West
Price was CA $1,511, price is now CA $1,246 per person
CA $1,246
per person
Sep 30 - Oct 5
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9/10 Wonderful! (1,938 reviews)
We really enjoyed our stay here and would be back for sure! Property is very clean and staff is really hospitable and accommodating.

Reviewed on Jul 8, 2026

Four Seasons Hotel St Louis

Four Seasons Hotel St Louis

5 out of 5
Downtown St. Louis
Price was CA $2,648, price is now CA $2,199 per person
CA $2,199
per person
Sep 30 - Oct 5
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9.4/10 Exceptional! (1,002 reviews)
It was ok

Reviewed on Jul 3, 2026

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 $154 per night from Aug 5 to Aug 6
CA $154
CA $179 total
Aug 5 - Aug 6
includes taxes & fees
8/10 Very good! (1,042 reviews)
"We had a unique experience living in apartment type room having kitchen, hall and bed together. Good for going longer days. Best part was having breakfast included."

Reviewed on Jul 10, 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
The price is CA $193 per night from Jul 22 to Jul 23
CA $193
CA $224 total
Jul 22 - Jul 23
includes taxes & fees
9.6/10 Exceptional! (1,216 reviews)
"We didn't like the menus for dinner, and there was never bacon for breakfast! The sausage was not tasty."

Reviewed on Jul 10, 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 $198 per night from Jul 17 to Jul 18
CA $198
CA $233 total
Jul 17 - Jul 18
includes taxes & fees
8.6/10 Excellent! (4,204 reviews)
"Great stay with amazing view of the Arch"

Reviewed on Jul 9, 2026

Hyatt Regency St. Louis at The Arch
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.
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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

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 $1,150 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.

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