Oakland City Vacations from $308
Book a Hotel + Flight or Car together to unlock savings
Your Oakland City Vacation
Our vacation packages to Oakland City let you customize your own adventure. Tailor your getaway to suit your needs and interests and make every moment count in this fabulous city. Need some inspiration on what to see or do first during your trip to Oakland City? Check off well-known attractions such as Oakland City University. Your perfect Oakland City vacation is only clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your style.
The Latest Oakland City vacation packages
Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Evansville East
$586
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Evansville (EVV)
8/10 Very Good! (1,005 reviews)
This is our 3rd or 4th stay at this HoJo. The facility is always clean and quiet. The showers are looking older with some cracking of the walls. No bugs!!
Reviewed on Oct 22, 2026
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See all available trips from Columbus to Oakland City
View all tripsStay near popular Oakland City attractions
Oakland City University
7.2/10 (47 reviews)
Explore the campus of Oakland City University, during your trip to Oakland City.
Oakland City Hotel Deals
Santas Lodge and Resort
91 W CHRISTMAS BLVD Santa Claus IN
Fully refundableReserve now, pay when you stay
$101 nightly
$113 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (463 reviews)
"Very clean place only complaint Is no fridge or microwave in rooms. Area night life none restaurants close at 8 on Fridays"
Reviewed on Oct 19, 2026
Fairfield Inn By Marriott Evansville East
7879 Eagle Crest Blvd Evansville IN
Fully refundableReserve now, pay when you stay
$84 nightly
$97 total
Nov 22 - Nov 23
Total with taxes and fees
Drury Inn & Suites Evansville East
100 Cross Pointe Blvd Evansville IN
Fully refundableReserve now, pay when you stay
$108 nightly
$124 total
Oct 27 - Oct 28
Total with taxes and fees
9.4/10 Exceptional! (1,004 reviews)
"Perfect place for our family for a weekend away for softball tournament"
Reviewed on Oct 22, 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.
Find the Best Oakland City Vacation Packages
Oakland City Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Evansville Regional Airport (EVV) |
Population | 2,400 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
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Frequently asked questions
How much does an Oakland City vacation package cost?
You'll find cheap prices from $308 on Expedia for your Oakland City escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Oakland City costs.
What are the cheapest months to go to Oakland City?
If you're hoping to score a cheap Oakland City vacation package, consider planning a trip in July, November and December. You're likely to find lower rates on flights and accommodations during these months — perfect for budget-conscious travelers.
How many days is enough for Oakland City?
The ideal duration for your Oakland City vacation depends on what you'd like to do and see. Usually, a few days to a week will give you enough time to check out all the major attractions and discover some hidden gems along the way.
How to find the best Oakland City package deals?
Use Expedia's filter tool to help you find some fabulous Oakland City package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Oakland City package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Oakland City vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights individually. Better still, you can personalize your Oakland City trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Oakland City?
Score fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Oakland City escape.
Does Expedia offer Book Now, Pay Later Oakland City vacation packages?
Set off on your perfect escape to Oakland City with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait until the next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to budget for your trip and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.