Oakland City Vacations from $636

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Quality Inn Evansville Eastland Area
Comfort Inn & Suites Evansville Airport
Towneplace Suites by Marriott Evansville Newburgh
SpringHill Suites by Marriott Newburgh Evansville
Hampton Inn Evansville/Airport
Don't see what you're looking for?
See all available trips from Columbus to Oakland City
View all trips

Discover the most popular places to visit in Oakland City

Oakland City Hotel Deals

Fairfield Inn By Marriott Evansville East

Fairfield Inn By Marriott Evansville East

3 out of 5
7879 Eagle Crest Blvd Evansville IN
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $97 total per night from May 24 to May 25
$97 total
May 24 - May 25
Total with taxes and fees
8.6/10 Excellent! (496 reviews)
Clean rooms and friendly front desk staff. Great price for for the room

Reviewed on May 10, 2026

Fairfield Inn By Marriott Evansville East
Drury Inn & Suites Evansville East

Drury Inn & Suites Evansville East

3 out of 5
100 Cross Pointe Blvd Evansville IN
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $145 total per night from May 19 to May 20
$145 total
May 19 - May 20
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
The rooms were clean and appeared well maintained. They are on the smaller side as are many of the amenities at this property. The staff was friendly and check in was quick and easy. The lobby is microscopic as is the breakfast/happy hour area. We have stayed at many Drury Inns over the years and ...

Reviewed on May 10, 2026

Drury Inn & Suites Evansville East
La Quinta Inn & Suites by Wyndham Evansville

La Quinta Inn & Suites by Wyndham Evansville

3 out of 5
8015 East Division Street Evansville IN
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $87 total per night from May 17 to May 18
$87 total
May 17 - May 18
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Breakfast was great! They kept it fresh and stocked up! The room was so nice. The only thing I can say is I wish they would’ve had the air conditioner on because it was hot when we got to the room.

Reviewed on May 14, 2026

La Quinta Inn & Suites by Wyndham Evansville
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

More vacations you might like

Frequently asked questions

How much does an Oakland City vacation package cost?
You'll find cheap prices from $636 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.