Chesterfield Vacations from $503

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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.
The Alexander, Autograph Collection

The Alexander, Autograph Collection

4 out of 5
Downtown Indianapolis
Price was $634, price is now $503 per person
$503
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
8.8/10 Excellent! (1,005 reviews)
Right in the perfect location to quickly go eat or shop. Room was immaculate. Beautifully decorated. Even had a hand held steamer for your wrinkled clothes. We will 100% stay at this wonderful hotel again!

Reviewed on May 29, 2026

Baymont by Wyndham Indianapolis South

Baymont by Wyndham Indianapolis South

2.5 out of 5
Price was $836, price is now $612 per person
$612
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Indianapolis (IND)
7.4/10 Good! (790 reviews)
Extremely friendly staff!

Reviewed on Jun 19, 2026

Comfort Inn Warren I-69

Comfort Inn Warren I-69

2.5 out of 5
Price was $1,007, price is now $789 per person
$789
per person
Jul 26 - Jul 29
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Indianapolis (IND)
7.6/10 Good! (298 reviews)
The staff was the most that stood out.

Reviewed on May 31, 2026

Bourbon Barrel Cabin on Lake Near Airport Downtown

Bourbon Barrel Cabin on Lake Near Airport Downtown

2 out of 5
Save 100% on your flight
Price was $2,237, price is now $1,820 per person
$1,820
per person
Jul 31 - Aug 5
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
No reviews
Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Price was $628, price is now $515 per person
$515
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
9.4/10 Exceptional! (1,078 reviews)
Wonderful experiance!. I had a small problem with the first room. Although clean, I found leftover socks on the floor. Called down to the front desk, was greeted with sincere apologies, a new room was immediately assigned, and they came up to my old room with the new room key... and carried my luggage to the UPGRADED new room... Love the white glove service, will definitely stay again!

Reviewed on Jun 19, 2026

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Discover the most popular places to visit in Chesterfield

Etowah Indian Mounds State Park, GA

Mounds State Park

4/5(6 reviews)

You can take time to visit Mounds State Park during your travels to Anderson. While in this family-friendly area, you can savor the top-notch restaurants.

Mounds State Park

Hoosier Park

4/5(76 reviews)

Why not try your luck with a visit to Hoosier Park during your travels in Anderson? While in this relaxing area, you can savor the top-notch restaurants.

Hoosier Park

Anderson Speedway

4/5(12 reviews)

You can take time to visit Anderson Speedway during your travels to Anderson. While in this relaxing area, you can savor the top-notch restaurants.

Anderson Speedway

Chesterfield Hotel Deals

Anderson Chesterfield Travel Inn

Anderson Chesterfield Travel Inn

2 out of 5
15701 W Commerce Rd Daleville IN
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $78 total per night from Jun 24 to Jun 25
$78 total
Jun 24 - Jun 25
Total with taxes and fees
7.8/10 Good! (271 reviews)
"Great staff, reasonably priced, nice stay. Happy to have stayed there."

Reviewed on May 26, 2026

Anderson Chesterfield Travel Inn
Wyndham Noblesville

Wyndham Noblesville

3 out of 5
13500 Tegler Drive Noblesville IN
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $129 total per night from Jul 5 to Jul 6
$129 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (1,496 reviews)
"Woke up to a bedbug crawling on me, took the bug down to staff to show them, got trash bags for all of our belongings. Upon check out the staff member asked for the bug to show management. We were told management would be contacting us that day, it’s been 3 days we’ve yet to hear from anyone, I’ve ..."

Reviewed on Jun 23, 2026

Wyndham Noblesville
Holiday Inn Express & Suites Indianapolis NE - Noblesville by IHG

Holiday Inn Express & Suites Indianapolis NE - Noblesville by IHG

2.5 out of 5
13625 Tegler Drive Noblesville IN
Fully refundable
$149 nightly
The price is $171 total per night from Jun 28 to Jun 29
$171 total
Jun 28 - Jun 29
Total with taxes and fees
9.4/10 Exceptional! (1,007 reviews)
"Didnt eat but yes i felt safe"

Reviewed on Jun 23, 2026

Holiday Inn Express & Suites Indianapolis NE - Noblesville by IHG
See all 154 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
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 $503 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.