Chesterfield Vacations from $171
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The Latest Chesterfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Larkspur Landing Extended Stay Suites St. Louis Riverport - Airport West
Riverport
$171
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
7.6/10 Good! (1,015 reviews)
This hotel was dirty. There was hair in the sheets, mold on the shower curtain, the ice buckets were missing that tops and dirty, etc. Do not recommend.
Reviewed on Sep 7, 2026
Remodeled and Inviting Free EV
$328
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9/10 Wonderful! (2 reviews)
It was nice to stay for a weekend but the neighborhood was nice I like the location where it wasn't too far from grocery stores food areas the only thing I was saying is it's nothing for the kids to do but overall I like it
Reviewed on Aug 7, 2026
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Super 8 by Wyndham Staunton
1527 Herman Rd Staunton IL
Fully refundableReserve now, pay when you stay
$78 nightly
$87 total
Sep 29 - Sep 30
Total with taxes and fees
Memorable Family experiences at The Castle of Palmyra.
Palmyra IL
10/10 Exceptional! (168 reviews)
"We loved everything about this property. Perfect and plenty of room. We played hide and seek and that was a very long game trying to find everyone."
Reviewed on Aug 25, 2026
Hampton Inn by Hilton Litchfield
11 Thunderbird Circle Litchfield IL
Fully refundableReserve now, pay when you stay
$110 nightly
$121 total
Sep 18 - Sep 19
Total with taxes and fees
9/10 Wonderful! (685 reviews)
"Good room and breakfast"
Reviewed on Sep 3, 2026
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 $171 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
