Chesterfield Vacations from $277

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,558 reviews)
Great place to stay.

Reviewed on Aug 12, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
8.2/10 Very Good! (760 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul 26, 2025

Holiday Inn Express & Suites St. Louis West - Fenton by IHG

Holiday Inn Express & Suites St. Louis West - Fenton by IHG

3 out of 5
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
great hotel clean and staff was fantasic

Reviewed on Aug 3, 2025

The Cheshire

The Cheshire

4 out of 5
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Bed and pillows where uncomfortable. Room and facilities were dirty. Parking was a joke due to there being 2 restaurants on the property as well so it was hard to find a spot as the hotel and restaurant shared the parking lot and garage but you had to pay to park if you stayed in the hotel.

Reviewed on Aug 3, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
8.4/10 Very Good! (1,001 reviews)
Clean. Quiet. Nice.

Reviewed on Aug 11, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all trips

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
$71 nightly
The price is $79 total per night from Aug 17 to Aug 18
$79 total
Aug 17 - Aug 18
Total includes taxes and fees
8.4/10 Very Good! (735 reviews)
"Receptionist was incredibly helpful, since I accidentally booked the wrong day."

Reviewed on Aug 4, 2025

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

Memorable Family experiences at The Castle of Palmyra.

Palmyra
9.8/10 Exceptional! (106 reviews)
"This is a great place to stay with a large family under one roof. We loved it and will come back again!"

Reviewed on Jul 25, 2025

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
$75 nightly
The price is $83 total per night from Aug 31 to Sep 1
$83 total
Aug 31 - Sep 1
Total includes taxes and fees
7.8/10 Good! (306 reviews)
Great front desk!
"We stayed here while exhibiting cattle at the Jersey county fair. The front desk was very welcoming and remembered us and our dog from last year!"

Reviewed on Jul 16, 2025

Super 8 by Wyndham Jerseyville
See all 23 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from $277 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.