Chesterfield Vacations from $412

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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
Price was $674, price is now $412 per person
$412
per person
Jan 30 - Feb 2
found 2 days ago
Roundtrip non-stop flight included
Baltimore (BWI) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
What stood out? Everything! The staff was friendly, the room was spacious and clean, and the breakfast was very good with plenty of variety.. also the lady working in the breakfast area stayed busy restocking breakfast items the whole time we ate. She was also very friendly. If we ever travel the area again we will definitely come back!

Reviewed on Dec 12, 2025

Hermann Grain Bins BNB

Hermann Grain Bins BNB

2 out of 5
Save 100% on your flight
Price was $1,492, price is now $1,064 per person
$1,064
per person
Jan 15 - Jan 19
found 22 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
2/10 (1 review)
Hotel Saint Louis, Autograph Collection

Hotel Saint Louis, Autograph Collection

4 out of 5
Downtown St. Louis
Price was $1,141, price is now $864 per person
$864
per person
Mar 5 - Mar 8
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to St. Louis (STL)
8.8/10 Excellent! (458 reviews)
Property and room was really nice. I will be staying here in the future

Reviewed on Nov 25, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was $881, price is now $671 per person
$671
per person
Mar 5 - Mar 8
found 2 hours ago
Roundtrip flight included
Baltimore (BWI) to St. Louis (STL)
8.2/10 Very Good! (779 reviews)
Just a really nice hotel tucked away from everything, but still close to get whereevre you need to go!

Reviewed on Oct 26, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Price was $528, price is now $420 per person
$420
per person
Jan 30 - Feb 2
found 2 days ago
Roundtrip non-stop flight included
Baltimore (BWI) to St. Louis (STL)
8.8/10 Excellent! (96 reviews)
Booked this hotel to catch a flight the next day. The hotel was clean and the breakfast was decent. The long term parking was confusing to find when I pulled in and cost more than was noted on Expedia. The shuttle driver was very nice and prompt and the shuttle was easy to find.

Reviewed on Dec 10, 2025

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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
$71 nightly
The price is $78 total per night from Jan 1 to Jan 2
$78 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.4/10 Very Good! (761 reviews)
The room was fine. The service was great. I would stay there again. The breakfast options weren't very good so we ate somewhere else.

Reviewed on Nov 22, 2025

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

Memorable Family experiences at The Castle of Palmyra.

Palmyra IL
9.8/10 Exceptional! (108 reviews)
My family of 9 adults met at The Castle and found The Castle and the furnishings were very fun and eccentric. It is a great place for a large family to gather with plenty of room and things to do like fishing, trolling around the pond, outdoor fire pit, walking, cooking, playing games and being outdoors. ...

Reviewed on Sep 28, 2025

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Memorable Family experiences at The Castle of Palmyra.
Hampton Inn by Hilton Litchfield

Hampton Inn by Hilton Litchfield

2.5 out of 5
11 Thunderbird Circle Litchfield IL
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $109 total per night from Dec 28 to Dec 29
$109 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (625 reviews)
Room was nice hallways are really cold. Like you are outside cold. Rooms have a lot of outside noise. Staff is very helpful. Breakfast was good.

Reviewed on Nov 28, 2025

Hampton Inn by Hilton Litchfield
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 $412 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.