Chesterfield Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

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Top Chesterfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Sep 27 - Oct 1
found 16 hours ago
Roundtrip non-stop flight included
Fort Wayne (FWA) to St. Louis (STL)
8.2/10 Very Good! (754 reviews)
The stay was too short

Reviewed on Jul. 2, 2025

Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
Save 100% on your flight
per person
Sep 27 - Oct 1
found 16 hours ago
Roundtrip non-stop flight included
Fort Wayne (FWA) to St. Louis (STL)
8.8/10 Excellent! (686 reviews)
The food in the restaurant was terrable. I had the meat balls and I could not eat them

Reviewed on Jun. 30, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
per person
Sep 27 - Oct 1
found 16 hours ago
Roundtrip non-stop flight included
Fort Wayne (FWA) to St. Louis (STL)
8.2/10 Very Good! (32 reviews)
Our comforter had blood stains on top. It was covered by a blanket topper but very much visible.

Reviewed on Jun. 28, 2025

The Cheshire

The Cheshire

4 out of 5
per person
Sep 27 - Oct 1
found 16 hours ago
Roundtrip non-stop flight included
Fort Wayne (FWA) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Would definitely go back

Reviewed on Jul. 12, 2025

Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
Save 100% on your flight
per person
Sep 27 - Oct 1
found 16 hours ago
Roundtrip non-stop flight included
Fort Wayne (FWA) to St. Louis (STL)
7.2/10 Good! (7 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on Jun. 8, 2025

Ready to book your vacation to Chesterfield?

 

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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
The price is CA $93 per night from Jul 20 to Jul 21
CA $93
CA $103 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (721 reviews)
"Clean and comfortable, with very nice and attentive staff."

Reviewed on Jul. 8, 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! (103 reviews)
Family vacation
"Castle is amazing, property is gorgeous and you have a private lake. Will definitely come back again."

Reviewed on Jun. 2, 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
The price is CA $100 per night from Aug 3 to Aug 4
CA $100
CA $111 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (301 reviews)
Decent for the price
"For the price this was a decent stay. All the staff were friendly and professional. Joe was especially helpful. The room could use some updating. The bed was comfortable. Conversations in the next room could be heard walls kind of thin bit overall no loud experiences."

Reviewed on Jul. 6, 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from CA $509 on Expedia, you'll be thrilled with how little a vacation to Chesterfield costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chesterfield?
If you'd like to score a cheap Chesterfield vacation package, consider visiting in January, February and November. You'll usually find better prices on hotels and flights during these months --- perfect for budget-conscious travellers.
How many days is enough for Chesterfield?
Generally, a handful of days is enough to tick off the main sights during your Chesterfield vacation. But if you want to have time to kick back or take day tours, think about extending your trip.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to find some of the best Chesterfield package deals. When you begin your search, just set your maximum budget and then sort 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 low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel 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're planning an impromptu Chesterfield vacation, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterfield?

  1. Choose your dates: The things you'd like to do in Chesterfield and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should factor in other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may arise during your trip to Chesterfield.
  3. Set the duration of your trip: Start by listing all the attractions you want to experience in Chesterfield. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the perfect 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.