Chesterfield Vacations from $295
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
- Comfort Inn Plainfield - Indianapolis Airport
Jan 21 - Jan 25Comfort Inn Plainfield - Indianapolis Airport + Flight
Plainfield4 nights2.5 star property7.8/10 - Good (701 reviews)"Blah"Reviewed November 8, 2026Roundtrip • Denver (DEN) - Indianapolis (IND)DEN - IND • Nonstop IND - DEN • Nonstop$383$295found 1 day agoper traveler - Omni Severin Hotel
Jan 11 - Jan 14Omni Severin Hotel + Flight
Downtown Indianapolis3 nights4.0 star property9.4/10 - Exceptional (1,533 reviews)Roundtrip • Denver (DEN) - Indianapolis (IND)DEN - IND • Nonstop IND - DEN • Nonstop$463$353found 1 day agoper traveler - The Westin Indianapolis
Jan 11 - Jan 14The Westin Indianapolis + Flight
Downtown Indianapolis3 nights4.0 star property8.8/10 - Excellent (1,000 reviews)Roundtrip • Denver (DEN) - Indianapolis (IND)DEN - IND • Nonstop IND - DEN • Nonstop$458$353found 1 day agoper traveler - Hyatt Place Indianapolis Downtown
Jan 11 - Jan 14Hyatt Place Indianapolis Downtown + Flight
Downtown Indianapolis3 nights3.0 star property9.0/10 - Wonderful (1,583 reviews)"Great hotel, services and staff, but there was a puddle of water from the toilet leaking and there was no bedding for the foldout couch. It took two hours to get bedding and for a maintenance person to come fix the leak."Reviewed November 7, 2026Roundtrip • Denver (DEN) - Indianapolis (IND)DEN - IND • Nonstop IND - DEN • Nonstop$414$319found 1 day agoper traveler - Hyatt House Indianapolis Downtown
Jan 11 - Jan 14Hyatt House Indianapolis Downtown + Flight
Downtown Indianapolis3 nights3.0 star property9.2/10 - Wonderful (1,260 reviews)Roundtrip • Denver (DEN) - Indianapolis (IND)DEN - IND • Nonstop IND - DEN • Nonstop$405$313found 1 day agoper traveler
Chesterfield Hotel Deals
Anderson Chesterfield Travel Inn
Anderson Chesterfield Travel Inn"Kind owners and quiet property. I've stayed here a few times now and have enjoyed both stays."
"Great staff, very clean and top notch breakfast!!!"
Holiday Inn Express Hotel & Suites ANDERSON NORTH by IHG
Holiday Inn Express Hotel & Suites ANDERSON NORTH by IHG"None"
Quality Inn & Suites Anderson I-69
Quality Inn & Suites Anderson I-69
"Ty"
"The staff was very accommodating to us will return again"
Fairfield Inn & Suites by Marriott Anderson
Fairfield Inn & Suites by Marriott Anderson
"Staff were the best in customer service."
Frequently Asked Questions
How much does a Chesterfield vacation package cost?
Offering excellent value package deals from $295 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.