Chesterfield Trips (flight + hotel)

Photo by Michelle E

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Top hotels in Chesterfield

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 P5,293 per night from Aug 24 to Aug 25
P5,293
P6,140 total
Aug 24 - Aug 25
includes taxes & fees
8/10 Very Good! (1,011 reviews)
"Very nice place to stay with a very friendly staff. My travels were for my mother’s funeral and your staff made it pretty easy for me. Thank you"

Reviewed on Aug 6, 2025

Sonesta ES Suites St. Louis - Chesterfield
Hyatt Place St. Louis/Chesterfield

Hyatt Place St. Louis/Chesterfield

3 out of 5
333 Chesterfield Center East, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is P6,794 per night from Sep 7 to Sep 8
P6,794
P7,881 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Great place to stay"

Reviewed on Aug 7, 2025

Hyatt Place 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 P6,794 per night from Aug 22 to Aug 23
P6,794
P8,012 total
Aug 22 - Aug 23
includes taxes & fees
8.4/10 Very Good! (3,913 reviews)
"Great hotel, very clean, smells nice. Housekeeping every day. Conveniently located next to shopping mall and golf course. I would come again."

Reviewed on Aug 6, 2025

Hyatt Regency St. Louis at The Arch
See all 2,056 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.

Popular places to visit

Gateway Arch featuring central business district, modern architecture and skyline

Gateway Arch

Visit the Museum of Westward Expansion, then ascend to the top of the tallest man-made monument in the US for breathtaking views of St. Louis.

Gateway Arch
St. Louis Zoo featuring a park, a bridge and a lake or waterhole

St. Louis Zoo

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

St. Louis Zoo

America's Center Convention Complex

Learn about the events happening at America's Center Convention Complex during your trip to St. Louis. Experience the area's acclaimed theater scene and great live music.

America's Center Convention Complex

What to do in Chesterfield

Adventure Valley Paintball Fun

Adventure Valley Paintball Park

P671
per adult
Adventure Valley Paintball Park
Wainwright Building

Landmarks Downtown-East Walking Tour

P989
per adult
Landmarks Downtown-East Walking Tour
Half day Trip Through Artistic Tapestry of St Louis

Half day Trip Through Artistic Tapestry of St Louis

P5,235
per adult
Half day Trip Through Artistic Tapestry of St Louis
See all activities in Chesterfield

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.

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