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
3 out of 5
15431 Conway Rd, Chesterfield, MO
The price is ₩128,188 per night from Jul 7 to Jul 8
₩128,188
₩148,683 total
Jul 7 - Jul 8
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"This property was able to accommodate me and family there was enough space for everyone. The kitchenette and two restrooms was much needed."

Reviewed on Jun 21, 2025

Sonesta ES Suites 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 ₩162,982 per night from Jun 30 to Jul 1
₩162,982
₩192,196 total
Jun 30 - Jul 1
includes taxes & fees
8.4/10 Very Good! (3,776 reviews)
"Next to arch and ballpark"

Reviewed on Jun 23, 2025

Hyatt Regency St. Louis at The Arch
Drury Plaza Hotel St. Louis at the Arch
Drury Plaza Hotel St. Louis at the Arch
3 out of 5
2 South 4th Street, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is ₩162,968 per night from Jun 30 to Jul 1
₩162,968
₩190,557 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (2,770 reviews)
Excellent stay
"Very impressed with this hotel. Check in was quick. Staff was very friendly. Free dinner buffet, free buffet breakfast and 3 free drinks a person at happy hour....impressive. Everything was great. Room was spacious and clean. Bed was comfortable. Zero complaints."

Reviewed on Jun 24, 2025

Drury Plaza Hotel St. Louis at the Arch
See all 2,063 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.

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.

Discover the most popular places to visit in Chesterfield

St. Louis Zoo

St. Louis Zoo

4.5/5(1,212 reviews)

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
Gateway Arch showing a city, a skyscraper and skyline

Gateway Arch

4.5/5(2,511 reviews)

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch
Seeing one of the largest hotels decked out in Rainbow lights in St. Louis is pretty awesome! Lots of food and drink options at this hotel & casino! #LifeAtExpedia

Horseshoe St. Louis Casino

4/5(14 reviews)

Why not roll the dice with a visit to Horseshoe St. Louis Casino during your time in St. Louis? Experience the area's fascinating museums or attend a baseball game.

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