Oakland City Vacations from $757

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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.
WoodSpring Suites Evansville East

WoodSpring Suites Evansville East

2.5 out of 5
Price was $830, price is now $757 per person
$757
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Evansville (EVV)
6.4/10 (236 reviews)
There was no breakfast

Reviewed on Sep 10, 2025

Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was $1,022, price is now $885 per person
$885
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Evansville (EVV)
8.6/10 Excellent! (498 reviews)
Overall, very good. The staff was very friendly. They are in the midst of renovating, and also recovering from a major lightning strike that took out a lot electrical equipment that is very expensive to replace. There is only one ice machine, which is located on the first floor.

Reviewed on Sep 28, 2025

New Harmony Inn Resort and Conference Center

New Harmony Inn Resort and Conference Center

3 out of 5
Price was $1,039, price is now $919 per person
$919
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Evansville (EVV)
9.2/10 Wonderful! (465 reviews)
Nice place to stay. We'll be back.

Reviewed on Sep 26, 2025

Holiday Inn Express & Suites Evansville North by IHG

Holiday Inn Express & Suites Evansville North by IHG

2.5 out of 5
Price was $923, price is now $829 per person
$829
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Evansville (EVV)
8.4/10 Very Good! (549 reviews)
It was good. They both of free Wi-Fi but it's a joke don't count on it for anything but your phone

Reviewed on Sep 30, 2025

FairBridge Inn Express Mount Vernon

FairBridge Inn Express Mount Vernon

2 out of 5
Price was $977, price is now $890 per person
$890
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Evansville (EVV)
6.2/10 (158 reviews)
It was older but functional for the visit. The bathroom door sticks. There was a stale smell in the room. The water pressure was strong and hot. I slept well.

Reviewed on May 26, 2025

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Discover the most popular places to visit in Oakland City

Oakland City University

4/5(25 reviews)

Explore the campus of Oakland City University, during your trip to Oakland City.

Oakland City University

Oakland City Hotel Deals

Oakland Courtyard

Oakland Courtyard

2 out of 5
1000 W Morton St, Oakland City, Oakland City, IN
$131 nightly
The price is $147 total per night from Nov 2 to Nov 3
$147 total
Nov 2 - Nov 3
Total with taxes and fees
Oakland Courtyard
Golf Course Views: Oakland City Retreat

Golf Course Views: Oakland City Retreat

3 out of 5
Oakland City
Get rates
Golf Course Views: Oakland City Retreat
Half-mi to Oakland City Golf Club: Sleek Apartment

Half-mi to Oakland City Golf Club: Sleek Apartment

3 out of 5
Oakland City
Get rates
Half-mi to Oakland City Golf Club: Sleek Apartment
See all 173 properties in Oakland City
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.

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 $757 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.