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 Cheshire
CA $1,513
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
Charming and quaint alternative to a Holiday Inn. It was renovated 10-15 years ago but not much care since then. The pool was allegedly open still (mid September) but when we looked out to go use it, there was debris in it and it wasn’t very inviting. The price was affordable and it was pet friendly, I only wish we could have experienced it during its heyday years ago when it was properly maintained and cleaned.
Reviewed on Sep 17, 2026
Ameristar Casino Resort and Spa
CA $1,668
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.6/10 Excellent! (1,033 reviews)
We only spent one night but the room was gorgeous the checking was easy and the employees were great. The food at the restaurants were also good and of course we did enjoy our time at the casino
Reviewed on Sep 15, 2026
Missouri Athletic Club
Downtown St. Louis
CA $1,355
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,003 reviews)
Lobby staff and restaurant staff were very nice and helpful. Steps away from the Dome which was very convenient for a concert venue.
Reviewed on Sep 15, 2026
Ready to book your vacation to Chesterfield?
Chesterfield Hotel Deals
Sonesta ES Suites St. Louis - Chesterfield
15431 Conway Rd Chesterfield MO
Fully refundableReserve now, pay when you stay
CA $159
CA $184 total
Sep 22 - Sep 23
includes taxes & fees
8/10 Very good! (1,062 reviews)
"The breakfast was inedible for us where the other times we've stayed it was okay. The toilet had issues and didn't flush and when we asked for someone to come fix it, they didn't come all day and we had to ask again when we got back in. The sink was also very slow. The shower was extremely slippery ..."
Reviewed on Sep 16, 2026
Drury Plaza Hotel St. Louis Chesterfield
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
CA $181
CA $210 total
Sep 22 - Sep 23
includes taxes & fees
9.6/10 Exceptional! (1,263 reviews)
"Facilities were excellent. The food and drink cards as well as breakfast were appreciated and very good."
Reviewed on Sep 16, 2026
Hyatt Place St. Louis/Chesterfield
333 Chesterfield Center East Chesterfield MO
Fully refundableReserve now, pay when you stay
CA $175
CA $203 total
Sep 20 - Sep 21
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"Awesome Staff"
Reviewed on Sep 16, 2026
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.
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.
The Factory
8.8/10 (47 reviews)
You can make plans for a show at The Factory on your trip to Chesterfield. Check out the shops and top-notch restaurants in this family-friendly area.
Sophia M. Sachs Butterfly House
8.8/10 (72 reviews)
Explore the great outdoors at Sophia M. Sachs Butterfly House, a lovely green space in Chesterfield. Discover the top-notch restaurants and great live music in this family-friendly area.
Babler State Park
8.6/10 (59 reviews)
You can take time to visit Babler State Park during your travels to Chesterfield. Attend a sporting event while in this family-friendly area or simply enjoy the top-notch restaurants.
Dr. Edmund A. Babler Memorial State Park
8.2/10 (57 reviews)
You can take time to visit Dr. Edmund A. Babler Memorial State Park during your travels to Chesterfield. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Myseum
8.4/10 (55 reviews)
You can spend an afternoon exploring the galleries in Myseum during your trip to Chesterfield. Experience the great live music or attend a sporting event in this family-friendly area.
Faust Park
8.8/10 (98 reviews)
Explore the great outdoors at Faust Park, a lovely green space in Chesterfield. Discover the great live music and shops in this family-friendly area.
Topgolf
You can take time to visit Topgolf during your travels to Chesterfield. Check out the shops and top-notch restaurants in this family-friendly area.
What to do in Chesterfield
St. Louis Ghost Tour: Sinister Sins & Shadows
CA $33
per adult
100% of travellers recommend
StL's Signature "Sights and Bites" - Private Tour in St. Louis
CA $242
per adult
Lemp Haunted Neighborhood Walking Tour
CA $35
per adult
84% of travellers recommend
Frequently asked questions
How much does a Chesterfield vacation package cost?
Offering great value package deals from CA $946 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?
- Choose your dates: The things you plan to do in Chesterfield and your favourite season can help you decide when to go.
- 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.
- 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.
- 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.
