Chesterfield Vacations from $569
Book a Hotel + Flight or Car together to unlock savings
Your Chesterfield Vacation
With all the details organized before you take off, our Chesterfield vacation packages mean you can simply focus on having a great time. Whether you stay in the neighborhood of Yorktown, which is great for golfing, or someplace else in town, this exciting city promises a wealth of discoveries. If your trip to Chesterfield includes a little sightseeing, don't miss much-loved attractions like Hoosier Park, Anderson Roll Arena and Mounds State Park. Expedia is here to help you escape your daily routine. Tailor your vacation to Chesterfield to suit your style of travel, whatever that may be!
The Latest Chesterfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Bloomington
Downtown Bloomington
$2,053
per person
Nov 24 - Nov 29
found 8 hours ago
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
8.6/10 Excellent! (1,008 reviews)
Great hotel located within easy walking distance to all the shops, restaurants and IU campus. Nice restaurant and bar in the lobby. The staff are friendly and helpful.
Reviewed on Sep 21, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all tripsStay near popular Chesterfield attractions
Labyrinth
Enjoy an outing to Labyrinth during your stay in Chesterfield. While you're in the area, stroll along the riverfront.
Chesterfield Hotel Deals
Anderson Chesterfield Travel Inn
15701 W Commerce Rd Daleville IN
Fully refundableReserve now, pay when you stay
$70 nightly
$78 total
Sep 29 - Sep 30
Total with taxes and fees
7.8/10 Good! (288 reviews)
"Clean and kind. Would definitely recommend."
Reviewed on Sep 19, 2026
Wyndham Noblesville
13500 Tegler Drive Noblesville IN
Fully refundableReserve now, pay when you stay
$94 nightly
$108 total
Oct 1 - Oct 2
Total with taxes and fees
Days Inn by Wyndham Muncie -Ball State University
3509 N Everbrook Ln Muncie IN
Fully refundableReserve now, pay when you stay
$61 nightly
$69 total
Oct 25 - Oct 26
Total with taxes and fees
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 |
Population | 2,500 |
Top Sights | Mounds State Park, Anderson Roll Arena and Hoosier Park |
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Frequently asked questions
How much does a Chesterfield vacation package cost?
Offering excellent value package deals from $569 on Expedia, you'll be pleasantly surprised at how much a vacation to Chesterfield costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chesterfield?
You're likely to find reduced prices and greater availability in December, January and February. Take a look at our cheap Chesterfield vacation packages and you could score some great off-season discounts.
How many days is enough for Chesterfield?
With a well-organized schedule, you can easily visit the top Chesterfield sights in a few days. But if you want to venture off the beaten track or go on day tours, consider booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Start your search for a Chesterfield package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Chesterfield package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chesterfield escape underway.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Chesterfield vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chesterfield?
Score amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Chesterfield break.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Chesterfield break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.