Chesterfield Vacation Packages
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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!
Top Chesterfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartments Near Northside
Near Northside
CA $1,331
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Indianapolis (IND)
8.8/10 Excellent! (8 reviews)
First of all there are no employees at the property. There is NO immediate help. I stayed for four days. I had to call a toll free number and wait for an operator to ask for more toilet paper on day 2 and then never got it before I left. The tv was busted in one of the bedrooms. They text me a code to get into the room, not the building. So after a 15-20 minute phone call I was able to get into the building. The property has approx 50+ 2BR 2BA apts on each floor. There are only 2 elevators right in the middle of the property with 25 apts or more on each side to the left or right. In other words, if you like walking a football field to your room, you’ll love this place. The rooms and bathrooms were very nice (xcept 4 the one TV). Every drawer was labeled with its contents in every room just in case you don’t know where something goes. Oh yea, forget about extra towels - there is a washer and dryer in the apts so you have to clean your own. Don’t forget the detergent because it’s not provided. One more fyi, since your entire stay revolves around the app and no one’s on site to help, if you lose your phone, you’ll never get back in your room again on your own. I hope I’ve been a big help in your decision to stay away from this dreadful place.
Reviewed on Aug 16, 2026
Ironworks Hotel Indy
CA $1,378
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Indianapolis (IND)
9.8/10 Exceptional! (2,081 reviews)
Everything excellent. Room spacious, clean, and cozy. Staff friendly and helpful. Property modern and safe, great area with lots of offerings for food and drink. First time visiting but definitely not last! Well done, Ironworks Indy!
Reviewed on Sep 4, 2026
Ready to book your vacation to Chesterfield?
Chesterfield Hotel Deals
Anderson Chesterfield Travel Inn
15701 W Commerce Rd Daleville IN
Fully refundableReserve now, pay when you stay
CA $97
CA $108 total
Sep 29 - Sep 30
includes taxes & fees
7.8/10 Good! (287 reviews)
"Great location"
Reviewed on Aug 25, 2026
Wyndham Noblesville
13500 Tegler Drive Noblesville IN
Fully refundableReserve now, pay when you stay
CA $126
CA $145 total
Sep 9 - Sep 10
includes taxes & fees
9/10 Wonderful! (1,472 reviews)
"Clean, nice breakfast."
Reviewed on Sep 5, 2026
Days Inn by Wyndham Muncie -Ball State University
3509 N Everbrook Ln Muncie IN
Fully refundableReserve now, pay when you stay
CA $85
CA $95 total
Oct 6 - Oct 7
includes taxes & fees
6.8/10 (959 reviews)
"Good hotel, will stay there again"
Reviewed on Sep 5, 2026
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.
Stay 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.
Frequently asked questions
How much does a Chesterfield vacation package cost?
You'll find cheap prices from CA $1,331 on Expedia for your Chesterfield escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
January, February and November are great times to search for cheap Chesterfield vacation packages. Travelling in quieter months means you can typically find lower prices on accommodations and flights.
How many days is enough for Chesterfield?
Generally, a few days is ideal for a Chesterfield vacation. With a well-planned itinerary, you can see all the top attractions like Mounds State Park, as well as 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 terrific Chesterfield package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Chesterfield package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chesterfield?
If you're planning an impromptu Chesterfield getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterfield?
- Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chesterfield.
- Plan your budget wisely: On top of the price of your hotel, you should consider other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Chesterfield.
- Decide how long to go for: Now that you're up to speed on Chesterfield, you can work out the right length of your break. Put together a draft plan and give yourself enough time for all the things you want to do.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chesterfield vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
