Chesterfield Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

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

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

Find the Best Chesterfield Vacation Packages

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 ₩93,217 per night from Jul 20 to Jul 21
₩93,217
₩103,452 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
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 ₩100,684 per night from Aug 3 to Aug 4
₩100,684
₩111,738 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
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
The price is ₩153,911 per night from Jul 31 to Aug 1
₩153,911
₩169,271 total
Jul 31 - Aug 1
includes taxes & fees
9/10 Wonderful! (594 reviews)
"Convient"

Reviewed on Jul 6, 2025

Hampton Inn by Hilton Litchfield
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.

Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices 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?
If you'd like to score a cheap Chesterfield vacation package, consider traveling in January, February and November. You'll generally find better rates on airfares and hotels during these months --- ideal for a budget-friendly break.
How many days is enough for Chesterfield?
The ideal duration of your Chesterfield vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to tick off all the major sights and discover some hidden gems along the way.
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 your bags packed. Your favorite time of year and the activities available will also help you decide when to escape to Chesterfield.
  2. Budget wisely: In addition to the cost of your accommodations, you'll need to consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could arise during your trip to Chesterfield.
  3. Set the duration of your trip: Start by listing all the attractions and activities you want to experience in Chesterfield. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, lock in the right 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.