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.
Alhonna Resort LLC
CA $949
per person
Sep 25 - Sep 27
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (323 reviews)
It is a perfect setup for families. We had a problem but it was immediately resolved. Staff is extremely professional.
Reviewed on Aug 7, 2026
Ready to book your vacation to Chesterfield?
Chesterfield Hotel Deals
Drury Plaza Hotel St. Louis Chesterfield
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
CA $181
CA $210 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (1,231 reviews)
"A very beautiful place. My son loved how they provided fountain soda and snacks."
Reviewed on Aug 7, 2026
Sonesta ES Suites St. Louis - Chesterfield
15431 Conway Rd Chesterfield MO
Fully refundableReserve now, pay when you stay
CA $155
CA $180 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very good! (1,050 reviews)
"I mistakenly left behind my work bag in the closet. Not only did the staff find it but they also made sure to get it back to me. Wonderful place with wonderful people!"
Reviewed on Aug 7, 2026
Holiday Inn Express & Suites St. Louis - Chesterfield by IHG
11 Arnage Boulevard Chesterfield MO
Fully refundable
CA $160
CA $186 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Overall we had a good stay"
Reviewed on Aug 7, 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.
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.
St. Louis Carousel
Enjoy an outing to St. Louis Carousel during your stay in Chesterfield. Check out the shops and top-notch restaurants 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.
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.
Taubman Prestige Outlets
8.4/10 (81 reviews)
During your trip to Chesterfield, you can search for that perfect souvenir at Taubman Prestige Outlets. Discover the top-notch restaurants and great live music in this family-friendly area.
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.
What to do in Chesterfield
St. Louis Ghost Tour: Sinister Sins & Shadows
CA $34
per adult
100% of travellers recommend
StL's Signature "Sights and Bites" - Private Tour in St. Louis
CA $246
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 $949 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.
