Chesterfield Vacations from $286

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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 Fontana Hotel

The Fontana Hotel

2.5 out of 5
Save 100% on your flight
Price was $396, price is now $286 per person
$286
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
8.2/10 Very Good! (952 reviews)
Breakfast ok , scrambled eggs were cold

Reviewed on May 5, 2026

Holiday Inn Express Hotel & Suites Greenwood by IHG

Holiday Inn Express Hotel & Suites Greenwood by IHG

2.5 out of 5
Save 100% on your flight
Price was $507, price is now $336 per person
$336
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9/10 Wonderful! (1,010 reviews)
They have a really nice breakfast.

Reviewed on May 6, 2026

Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $672, price is now $461 per person
$461
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.4/10 Exceptional! (949 reviews)
Best staff! They went above and beyond to make sure I was taken care of!

Reviewed on May 6, 2026

The Alexander

The Alexander

4 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $764, price is now $529 per person
$529
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
8.8/10 Excellent! (1,001 reviews)
The whole staff is very attentive, very friendly when you stay you have to spend time in the bar (Plat 99) as the drinks and staff are great!

Reviewed on May 4, 2026

Staybridge Suites Indianapolis-Fishers by IHG

Staybridge Suites Indianapolis-Fishers by IHG

3 out of 5
Save 100% on your flight
Price was $634, price is now $451 per person
$451
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
8.6/10 Excellent! (792 reviews)
This is perfect do families. Great suites, comfortable beds, great breakfast and accommodating staff. What more could you ask for when traveling with family?

Reviewed on Apr 4, 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 family-friendly 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 May 10 to May 11
$78 total
May 10 - May 11
Total with taxes and fees
7.8/10 Good! (268 reviews)
Friendly welcoming staff, clean and comfortable room

Reviewed on Apr 15, 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
$111 nightly
The price is $128 total per night from May 10 to May 11
$128 total
May 10 - May 11
Total with taxes and fees
9/10 Wonderful! (1,472 reviews)
I liked having real plates, silverware and cups at breakfast. The cleaning staff blocked the elevator with their cart and only one elevator was working. Minor inconvenience. Overall it was very acceptable.

Reviewed on May 8, 2026

Wyndham Noblesville
Embassy Suites by Hilton Noblesville Indianapolis Convention Center

Embassy Suites by Hilton Noblesville Indianapolis Convention Center

3.5 out of 5
13700 Conference Center Drive South Noblesville IN
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $178 total per night from May 26 to May 27
$178 total
May 26 - May 27
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
The room was perfect except for the view I didn’t like facing that view but I will pick a better view

Reviewed on May 4, 2026

Embassy Suites by Hilton Noblesville Indianapolis Convention Center
See all 153 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 $286 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.