Oakland City Vacations from $429

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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.
Best Budget Inn

Best Budget Inn

2.5 out of 5
Price was $460, price is now $429 per person
$429
per person
Aug 5 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Evansville (EVV)
5.2/10 (247 reviews)
The room was okay in and of itself. People that run it were very nice. Three major problems. First the main heating unit didn't work They had a very small heater that sucked. I had to go out and buy one. Secondly, the power kept going out. I couldn't use two heaters and watch TV at the same time. Power went out five times. I had to settle for not being able to watch TV or freeze my butt off. Third problem was that the toilet became stopped up and I couldn't get it unclogged with the plunger that was in the room. Bottom line is that they should have offered me another room. There were more empty rooms available but they didn't mention moving me to one that at least had heat. Before I would stay there again I would make sure that the room was properly heated and that I could watch TV and not have to worry about the power going out

Reviewed on Jan 9, 2026

Holiday Inn Express Evansville West by IHG

Holiday Inn Express Evansville West by IHG

2.5 out of 5
Price was $612, price is now $568 per person
$568
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Evansville (EVV)
8.6/10 Excellent! (582 reviews)
The morning staff were very friendly and helpful. The lady at the desk helped me find an ice machine. A nice gentleman and I chatted about my love for the cinnamon rolls you can only find at their hotels. And the breakfast attendant kept everything clean, and even packed up an extra cinnamon roll for us to take along. We left there ready for a good day.

Reviewed on Jun 24, 2026

Baymont by Wyndham Evansville North/Haubstadt

Baymont by Wyndham Evansville North/Haubstadt

2.5 out of 5
Price was $521, price is now $493 per person
$493
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Evansville (EVV)
7.6/10 Good! (1,001 reviews)
Easy check in. Very clean facility and room. Would stay again. Won’t beat what is offered for the price. Only negative would be to add a few more breakfast items.

Reviewed on Jun 26, 2026

Howard Johnson by Wyndham Evansville East

Howard Johnson by Wyndham Evansville East

2.5 out of 5
Price was $521, price is now $493 per person
$493
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Evansville (EVV)
8/10 Very Good! (1,008 reviews)
Everything was clean, the beds are comfy compared to other places we've stayed. Staff was all friendly & helpful.

Reviewed on Jun 23, 2026

Super 8 by Wyndham Evansville North

Super 8 by Wyndham Evansville North

2 out of 5
Price was $501, price is now $477 per person
$477
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Evansville (EVV)
7.8/10 Good! (536 reviews)
Breakfast was nothing special.

Reviewed on Jun 16, 2026

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Stay near popular Oakland City attractions

Oakland City University

7.2/5 (47 reviews)
Explore the campus of Oakland City University, during your trip to Oakland City.
See properties

Oakland City Hotel Deals

Oakland Courtyard

Oakland Courtyard

2 out of 5
1000 W Morton St, Oakland City Oakland City IN
$159 nightly
The price is $178 total per night from Jun 30 to Jul 1
$178 total
Jun 30 - Jul 1
Total with taxes and fees
Oakland Courtyard
Santas Lodge and Resort

Santas Lodge and Resort

2.5 out of 5
91 W CHRISTMAS BLVD Santa Claus IN
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $203 total per night from Jul 21 to Jul 22
$203 total
Jul 21 - Jul 22
Total with taxes and fees
8/10 Very Good! (340 reviews)
"The whole place was very clean and the staff was incredibly friendly and helpful! It is an older facility but is in pretty good shape, considering. The breakfast was fresh and yummy. Honestly, my only complaint is that the hot tub was not very hot at all. Otherwise, the place was lovely!!"

Reviewed on Jun 29, 2026

Santas Lodge and Resort
Comfort Inn Ferdinand

Comfort Inn Ferdinand

2.5 out of 5
123 Scenic Hills Court Ferdinand IN
Fully refundable
$131 nightly
The price is $147 total per night from Jul 26 to Jul 27
$147 total
Jul 26 - Jul 27
Total with taxes and fees
8.4/10 Very Good! (682 reviews)
"It met all our expectations for our two day stay."

Reviewed on Jun 29, 2026

Comfort Inn Ferdinand
See all 179 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.

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 $429 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.