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.
Courtyard by Marriott Indianapolis at the Capitol

Courtyard by Marriott Indianapolis at the Capitol

3 out of 5
Downtown Indianapolis
per person
Aug 12 - Aug 14
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Indianapolis (IND)
8.6/10 Excellent! (732 reviews)
clean and quiet room. convenient location

Reviewed on Jun. 30, 2025

Hampton Inn Indianapolis Downtown Across from Circle Centre

Hampton Inn Indianapolis Downtown Across from Circle Centre

2.5 out of 5
Downtown Indianapolis
per person
Aug 12 - Aug 14
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Indianapolis (IND)
8.6/10 Excellent! (1,006 reviews)
The entire staff was generous & professional. Our room was super clean & the bed was comforting. Our stay was a wonderful experience & we would highly recommend this hotel.

Reviewed on Jul. 4, 2025

Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
per person
Aug 12 - Aug 14
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Indianapolis (IND)
9.4/10 Exceptional! (452 reviews)
Great hotel to stay in. Everything was very clean and the food at the restaurant and bar area were delicious. Room was very clean but the only downside is there is very little sink space. I ended up keeping make up and toiletries bag on the nightstand. Otherwise our stay was great!! Walking distance to almost everything. If you’re there for a game it’s super close to every stadium.

Reviewed on Jul. 5, 2025

Holiday Inn Indianapolis Downtown by IHG

Holiday Inn Indianapolis Downtown by IHG

3 out of 5
Downtown Indianapolis
per person
Aug 12 - Aug 14
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Indianapolis (IND)
8/10 Very Good! (1,008 reviews)
Staff was very friendly and accomodating.

Reviewed on Jun. 24, 2025

Aloft Indianapolis Downtown

Aloft Indianapolis Downtown

3 out of 5
Downtown Indianapolis
per person
Aug 12 - Aug 14
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Indianapolis (IND)
9.2/10 Wonderful! (34 reviews)
Super friendly staff and valet service.

Reviewed on Jul. 3, 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 $95 per night from Jul 31 to Aug 1
CA $95
CA $107 total
Jul 31 - Aug 1
includes taxes & fees
7.6/10 Good! (242 reviews)
"Great place and great people"

Reviewed on May 26, 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 $137 per night from Aug 4 to Aug 5
CA $137
CA $157 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (1,192 reviews)
"Nice room and comfortable stay. Also appreciated being allowed to check in early"

Reviewed on Jul. 3, 2025

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
The price is CA $154 per night from Aug 4 to Aug 5
CA $154
CA $177 total
Aug 4 - Aug 5
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Loved it!!!"

Reviewed on Jun. 29, 2025

Holiday Inn Express & Suites Indianapolis NE - Noblesville by IHG
See all 124 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from CA $780 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.