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.
Crowne Plaza Indianapolis-Airport by IHG

Crowne Plaza Indianapolis-Airport by IHG

3.5 out of 5
Wayne
Price was CA $1,094, price is now CA $871 per person
CA $871
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
8.8/10 Excellent! (1,004 reviews)
Friendly staff, clean rooms, cleanliness of hotel overall. Onsite, free parking

Reviewed on Aug. 20, 2025

Hampton Inn Indianapolis Downtown IUPUI

Hampton Inn Indianapolis Downtown IUPUI

2.5 out of 5
Downtown Indianapolis
Price was CA $1,106, price is now CA $876 per person
CA $876
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
8.8/10 Excellent! (669 reviews)
super staff, fast elevators, clean

Reviewed on Aug. 19, 2025

Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Price was CA $1,299, price is now CA $1,035 per person
CA $1,035
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
9.4/10 Exceptional! (574 reviews)
Excellent property but loud outside at night and construction nearby made maneuvering to/from property difficult

Reviewed on Aug. 24, 2025

Homewood Suites by Hilton Indianapolis Downtown IUPUI

Homewood Suites by Hilton Indianapolis Downtown IUPUI

3 out of 5
Downtown Indianapolis
Price was CA $1,152, price is now CA $923 per person
CA $923
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
9.2/10 Wonderful! (572 reviews)
Amazing staff!! Made my children feel so welcome, this is a family friendly place to stay for sure.

Reviewed on Aug. 21, 2025

Fairfield Inn & Suites by Marriott Indianapolis Downtown

Fairfield Inn & Suites by Marriott Indianapolis Downtown

3 out of 5
Downtown Indianapolis
Price was CA $1,326, price is now CA $1,073 per person
CA $1,073
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
9/10 Wonderful! (1,019 reviews)
Super friendly staff. Conveniently close the museum and zoom. Walkable to downtown. But I was surprised the city is not vivid. Not much life!

Reviewed on Aug. 23, 2025

Ready to book your vacation to Chesterfield?

 

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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
The price is CA $97 per night from Sep 16 to Sep 17
CA $97
CA $108 total
Sep 16 - Sep 17
includes taxes & fees
7.6/10 Good! (254 reviews)
"Facility was clean and situated in a quiet area away from the Interstate. I plan to stay with them again this time next year. Highly recommend."

Reviewed on Aug. 21, 2025

Anderson Chesterfield Travel Inn
Wyndham Noblesville

Wyndham Noblesville

3 out of 5
13500 Tegler Drive, Noblesville, IN
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Sep 23 to Sep 24
CA $139
CA $160 total
Sep 23 - Sep 24
includes taxes & fees
8.8/10 Excellent! (1,270 reviews)
"Have stayed at this facility numerous times and it is always top-notch. Friendly helpful staff. Clean rooms and bathrooms."

Reviewed on Aug. 24, 2025

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
The price is CA $199 per night from Sep 1 to Sep 2
CA $199
CA $228 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
5 stars
"Great rooms, complementary happy hour, very nice employees- would definitely stay again"

Reviewed on Aug. 22, 2025

Embassy Suites by Hilton Noblesville Indianapolis Convention Center
See all 123 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from CA $871 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.