Chesterfield Vacations from $235

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
HoteLumiere at the Arch - A Caesars Rewards Destination

HoteLumiere at the Arch - A Caesars Rewards Destination

4 out of 5
Downtown St. Louis
Price was $290, price is now $235 per person
$235
per person
Jun 24 - Jun 26
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
6.8/10 (1,000 reviews)
Definitely needs some updates and a little TLC

Reviewed on Mar 9, 2026

The Westin St. Louis

The Westin St. Louis

4.5 out of 5
Downtown St. Louis
Price was $542, price is now $421 per person
$421
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.6/10 Excellent! (1,007 reviews)
Wonderful first time stay at this hotel. We will be back. Only suggestion would be for the meat selection at breakfast buffets it was slightly over cooked each day.

Reviewed on Apr 2, 2026

Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
Save 100% on your flight
Price was $640, price is now $498 per person
$498
per person
May 4 - May 8
found 5 hours ago
Roundtrip non-stop flight included
Washington (WAS) to St. Louis (STL)
8.8/10 Excellent! (11 reviews)
Clean room nice area

Reviewed on Feb 1, 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was $617, price is now $485 per person
$485
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.4/10 Very Good! (1,000 reviews)
Excellent place to stay on our trip West. Rooms are amazing and spacious, great river view. Quiet, clean and comfortable. Good, safe location and much to do. Easy parking and very friendly staff. Great restaurant choices. We will be back.

Reviewed on Apr 2, 2026

Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
Price was $570, price is now $448 per person
$448
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.8/10 Excellent! (731 reviews)
Did not eat there breakfast use gym but all was good especially the staff

Reviewed on Mar 28, 2026

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Chesterfield Hotel Deals

Super 8 by Wyndham Staunton

Super 8 by Wyndham Staunton

2 out of 5
1527 Herman Rd Staunton IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Apr 5 to Apr 6
$90 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (777 reviews)
Very nice, good breakfast and comfortable beds

Reviewed on Mar 31, 2026

Super 8 by Wyndham Staunton
Memorable Family experiences at The Castle of Palmyra.

Memorable Family experiences at The Castle of Palmyra.

Palmyra IL
10/10 Exceptional! (163 reviews)
First of all, the property is lovely. Debbi is an amazing property manager and extremely helpful! The kitchen is outfitted with everything you could imagine you might need. Lots of places to gather and just be together.

Reviewed on Jan 6, 2026

Get rates
Memorable Family experiences at The Castle of Palmyra.
Super 8 by Wyndham Jerseyville

Super 8 by Wyndham Jerseyville

2 out of 5
1303 State Highway 109 Jerseyville IL
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $100 total per night from Apr 13 to Apr 14
$100 total
Apr 13 - Apr 14
Total with taxes and fees
8/10 Very Good! (340 reviews)
Great experience, friendly staff, clean rooms

Reviewed on Mar 22, 2026

Super 8 by Wyndham Jerseyville
See all 27 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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from $235 on Expedia for your Chesterfield break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
You can generally find lower prices and greater availability in November, December and January. Browse our cheap Chesterfield vacation packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-planned schedule, you can easily tick off the top Chesterfield attractions in a few days. But if you want to discover hidden gems or go on day trips, consider booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Use Expedia's handy filters to help you find some tempting Chesterfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Chesterfield package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
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 separately. Better still, you can customize your Chesterfield getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Chesterfield?
If you're planning a spur-of-the-moment Chesterfield vacation, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Chesterfield?

  1. Choose when to get away: Check your schedule and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Chesterfield.
  2. Set a budget: Consider costs such as transportation, flights and meals when calculating how much to put aside for your trip to Chesterfield. Then, choose a hotel that fits your budget, whether that's an economical stay or a lavish getaway.
  3. Organize your Chesterfield getaway with Expedia's trip planning tool: Search for and book accommodations and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Chesterfield together.
  4. Decide how long to go away for: Now that you know more about Chesterfield, you can figure out the perfect length of your vacation. Create a rough itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Chesterfield vacation package.
  6. Add on experiences and excursions: Read our travel guide to find some awesome things to do in Chesterfield. Book tickets or make reservations in advance to save time and skip the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Chesterfield break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.