Oaklandon Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Oaklandon Vacation

Book a custom vacation package to Oaklandon and prepare to experience this fascinating city how you want. Consider spending time in the neighborhood of Castleton, which is good for shopping and tons more. If sightseeing is part of the plan during your trip to Oaklandon, stop by popular attractions like Fort Harrison State Park, Castleton Square and Topgolf. No matter your travel plans or the size of your budget, putting together a tailored Oaklandon vacation is easy with Expedia.

Top Oaklandon Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Fourwinds Lakeside Inn & Marina

Fourwinds Lakeside Inn & Marina

3 out of 5
per person
Aug 22 - Aug 25
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
8.2/10 Very Good! (677 reviews)
Nice clean hotel. Staff is great

Reviewed on Jul. 7, 2025

Days Inn by Wyndham Cloverdale Greencastle

Days Inn by Wyndham Cloverdale Greencastle

2 out of 5
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9.4/10 Exceptional! (367 reviews)
Excellent. Don’t pass up. I usually stay at more expensive hotels for comfort and cleanliness. No need to spend more in this area if all you want is a simple clean room with excellent amenities.

Reviewed on Jul. 9, 2025

TownePlace Suites by Marriott Indianapolis Downtown

TownePlace Suites by Marriott Indianapolis Downtown

3 out of 5
Downtown Indianapolis
per person
Aug 22 - Aug 25
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9.4/10 Exceptional! (662 reviews)
Excellent all across the board perfect for spontaneous trip!

Reviewed on Jul. 7, 2025

Ready to book your vacation to Oaklandon?

 

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Oaklandon Hotel Deals

Wyndham Indianapolis Airport
Wyndham Indianapolis Airport
3.5 out of 5
2544 Executive Dr, Indianapolis, IN
The price is CA $150 per night from Aug 4 to Aug 5
CA $150
CA $175 total
Aug 4 - Aug 5
includes taxes & fees
7.8/10 Good! (1,249 reviews)
Enjoyable weekend stay
"The check in with Jeremy was smooth. Once in the room there is a card to let you know housekeeping will be every other day unless requested otherwise which is nice for those of us who don’t need the sheets and towels switched every day. My room had a fridge and microwave (yay). Only down side was ..."

Reviewed on Jul. 7, 2025

Wyndham Indianapolis Airport
Ironworks Hotel Indy
Ironworks Hotel Indy
4 out of 5
2721 E 86th Street, Indianapolis, IN
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from Jul 13 to Jul 14
CA $245
CA $286 total
Jul 13 - Jul 14
includes taxes & fees
9.6/10 Exceptional! (1,499 reviews)
"Perfect place to stay!"

Reviewed on Jul. 7, 2025

Ironworks Hotel Indy
Sheraton Indianapolis Hotel at Keystone Crossing
Sheraton Indianapolis Hotel at Keystone Crossing
4 out of 5
8787 Keystone Crossing, Indianapolis, IN
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jul 13 to Jul 14
CA $150
CA $176 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (1,260 reviews)
Retired Army!
"It was a good one"

Reviewed on Jul. 6, 2025

Sheraton Indianapolis Hotel at Keystone Crossing
See all 2,373 properties in Oaklandon
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

Discover the most popular places to visit in Oaklandon

Indianapolis Motor Speedway which includes interior views

Indianapolis Motor Speedway

4.5/5(26 reviews)

Buckle up at the world’s most famous speedway and experience G-force thrills usually reserved for race car drivers.

Indianapolis Motor Speedway
Indiana Convention Center

Indiana Convention Center

4/5(24 reviews)

During your trip, find out what's happening at Indiana Convention Center, a top convention center in Indianapolis. Experience the area's acclaimed theater scene and entertainment choices.

Indiana Convention Center
Gainbridge Fieldhouse

Gainbridge Fieldhouse

3.5/5(5 reviews)

Catch an event at Gainbridge Fieldhouse during your trip to Indianapolis. Experience the area's entertainment choices or attend a sporting event.

Gainbridge Fieldhouse

What to do in Oaklandon

Step into the shadows and discover the haunting tales of our city's past.

Indianapolis Ghosts: Haunts, Spirits, and Phantoms Walking Tour

CA $44
per adult
Indianapolis Ghosts: Haunts, Spirits, and Phantoms Walking Tour
Group with axes for throwing in Indianapolis

30-Minute Walk-In Axe Throwing Experience Indianapolis

CA $30
per adult
100% of travellers recommend
30-Minute Walk-In Axe Throwing Experience Indianapolis
Bike and Brews Seeing Indy on an E-Bike

Bike and Brews Seeing Indy on an E-Bike

CA $192
per adult
Bike and Brews Seeing Indy on an E-Bike
See all activities in Oaklandon

Frequently asked questions

How much does an Oaklandon vacation package cost?
You'll find cheap prices from CA $544 on Expedia for your Oaklandon break. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Oaklandon costs.
What are the cheapest months to go to Oaklandon?
Plan your trip for the off-peak season and you're likely to score cheap Oaklandon vacation packages. Keep in mind that school vacation periods and major festivals and events can impact prices, so do a little research before booking.
How many days is enough for Oaklandon?
We'd suggest booking an Oaklandon vacation for at least 2 days. This will give you plenty of time to check off key attractions including Geist Reservoir and Fort Benjamin Harrison Golf Course, and explore neighbourhoods like Castleton and Ivy Hills. You could even make time for a day trip or two outside of Oaklandon.
How to find the best Oaklandon package deals?
Landing a cheap Oaklandon package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Oaklandon package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book an Oaklandon vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can personalize your Oaklandon escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Oaklandon?
If you have your Oaklandon vacation dates confirmed, book as soon as you can to bag some unbeatable deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Oaklandon?

  1. Choose your travel dates: What you plan to do in Oaklandon and your favourite season will help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to activities and flights. Your accommodations will probably be the largest expense during your trip to Oaklandon.
  3. Decide how long to go away for: Now that you're up to speed on Oaklandon, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick an Oaklandon 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.