Chesterfield Vacations

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Find the Best Chesterfield Vacation Packages

Chesterfield Hotel Deals

Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO
Fully refundableReserve now, pay when you stay
AED 400
AED 464 total
27 Sep - 28 Sep
includes taxes & fees
Sonesta ES Suites St. Louis - Chesterfield
Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
AED 477
AED 554 total
25 Oct - 26 Oct
includes taxes & fees
9.6/10 Exceptional! (1,271 reviews)
"The hotel staff were friendly, breakfast and dinner were tasty, The 3 free beverages with dinner were an extra nice surprise. Having the option to decline housekeeping during my stay shows they are eco friendly."

Reviewed on 25 September 2026

Drury Plaza Hotel St. Louis Chesterfield
Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

11 Arnage Boulevard Chesterfield MO
Fully refundable
AED 408
AED 474 total
25 Oct - 26 Oct
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Very clean, super friendly staff, close to lots of restaurants and so nice because it was so close to the district/the Factory (concert venue)."

Reviewed on 25 September 2026

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG
See all 2,299 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.

Stay near popular Chesterfield attractions

The Factory

8.8/10 (47 reviews)
The Factory hosts a diverse range of concerts in an intimate yet spacious setting with excellent acoustics. Arrive early to explore this modern venue with comfortable seating and multiple bars before performances begin.
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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.
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Sophia M. Sachs Butterfly House

8.8/10 (72 reviews)
Step into a tropical paradise where over 1,500 butterflies flutter freely through an 8,000-square-foot glass conservatory. Morning visits offer the best chance to witness these delicate creatures at their most active.
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Babler State Park

8.6/10 (59 reviews)
This 2,500-acre natural haven offers miles of forest trails through scenic Ozark landscapes. Explore limestone valleys, spot native wildlife, and enjoy camping under the stars in Missouri's tranquil wilderness.
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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.
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Topgolf

This high-tech golf venue blends precision tracking technology with casual fun for all skill levels. Enjoy climate-controlled hitting bays while savoring chef-prepared dishes delivered to your game area.
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Faust Park

8.8/10 (98 reviews)
Step into Faust Park's historic village and explore 19th-century buildings that showcase Missouri's rich heritage. The park's butterfly house and antique carousel offer enchanting experiences for the whole family.
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Myseum

8.4/10 (55 reviews)
Myseum offers over 30 hands-on exhibits where children can dig for dinosaurs or play veterinarian. Families can spend 2-3 hours exploring the interactive science and art concepts in this creative learning space.
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Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals 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 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 favorite 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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