Chesterfield Vacations

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Find the Best Chesterfield Vacation Packages

Chesterfield Hotel Deals

Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
NT$4,164
NT$4,830 total
Sep 7 - Sep 8
includes taxes & fees
Drury Plaza Hotel St. Louis Chesterfield
Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO
Fully refundableReserve now, pay when you stay
NT$3,376
NT$3,916 total
Aug 25 - Aug 26
includes taxes & fees
8/10 Very Good! (1,041 reviews)
"My husband and I travel across the country about 2 x year to visit our daughter. This Sonesta ES Suites is the one return place that we’ve come back to. The space is awesome with a full refrigerator and plenty of room to spread out. The hotel is truly pet friendly and staff are great- not to mention ..."

Reviewed on 2026/8/14

Sonesta ES Suites 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
NT$3,570
NT$4,154 total
Sep 13 - Sep 14
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Clean, spacious rooms. Beds were comfortable."

Reviewed on 2026/8/10

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG
See all 2,289 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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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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St. Louis Carousel

This century-old St. Louis Carousel features 60+ hand-carved wooden horses and deer in a climate-controlled pavilion. Enjoy nostalgic organ music while admiring the intricate craftsmanship of this rare antique treasure.
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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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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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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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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.
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Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination on Expedia. But how much your vacation to Chesterfield costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chesterfield?
December, January and February are great times to search for cheap Chesterfield vacation packages. Traveling in less busy periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Chesterfield?
With about 2 days, you'll have plenty of time to enjoy popular neighborhoods such as Clarkson Valley and Winchester during your Chesterfield vacation. Be sure to also add Myseum and The Factory to your sightseeing itinerary. In the mood for more adventures? Consider exploring outside of Chesterfield on day trips and tours.
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'd like to check out sights like The Factory and Chesterfield Sports Fusion, or venture off the beaten track, you'll have plenty to do on your Chesterfield vacation.
How to find the best Chesterfield package deals?
Begin your search for a Chesterfield package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesterfield package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chesterfield adventure underway.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a customized Chesterfield vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Chesterfield?
If you've got your Chesterfield travel dates finalized, book as early as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Chesterfield?
  1. Choose your dates: What you plan to do in Chesterfield and your favorite season can help you decide when to get away.
  2. Set a budget: Consider expenses like transportation, flights and meals when calculating how much to set aside for your trip to Chesterfield. Then, choose a hotel that works with your budget, whether that's an affordable option or a high-end retreat.
  3. Decide your trip length: Think about how long you'd like to spend exploring Chesterfield. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, book 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.