Oakland City Vacations from $782

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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.
PT6 INN

PT6 INN

2.5 out of 5
Price was $810, price is now $782 per person
$782
per person
Jun 28 - Jul 2
found 11 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Evansville (EVV)
4.6/10 (105 reviews)
Staff was nice and friendly

Reviewed on Nov 12, 2025

New Harmony Inn Resort and Conference Center

New Harmony Inn Resort and Conference Center

3 out of 5
Price was $976, price is now $927 per person
$927
per person
Jun 28 - Jul 2
found 11 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Evansville (EVV)
9/10 Wonderful! (517 reviews)
We had problems with the keycards and the door mechanism. There wasn’t enough staff to help us with the problem or even come to the room to check it out. The pool area was pretty poor shape. The town and the food was wonderful.

Reviewed on Apr 27, 2026

Quality Inn Grayville

Quality Inn Grayville

2.5 out of 5
Price was $861, price is now $820 per person
$820
per person
Jun 28 - Jul 2
found 11 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Evansville (EVV)
7.8/10 Good! (125 reviews)
Room was very clean .

Reviewed on Dec 28, 2025

Hampton Inn Evansville/Airport

Hampton Inn Evansville/Airport

2.5 out of 5
Price was $1,017, price is now $977 per person
$977
per person
Jun 28 - Jul 2
found 11 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Evansville (EVV)
9.2/10 Wonderful! (582 reviews)
Room was clean. Breakfast was as expected for a Hampton except coffee was weak, seemed watered down. Staff was awesome.

Reviewed on May 3, 2026

Envi Boutique Hotel Henderson-Evansville South

Envi Boutique Hotel Henderson-Evansville South

3 out of 5
Price was $925, price is now $895 per person
$895
per person
Jun 28 - Jul 2
found 11 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Evansville (EVV)
8/10 Very Good! (303 reviews)
Very clean and elegant would highly recommend even for a weekend getaway perfect !!!

Reviewed on Apr 19, 2026

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Discover the most popular places to visit in Oakland City

Oakland City University

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

Oakland City University

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
$87 nightly
The price is $100 total per night from May 17 to May 18
$100 total
May 17 - May 18
Total with taxes and fees
8.6/10 Excellent! (495 reviews)
The staff was very friendly and didn’t try to rush you before checkout I’ll stay there next time I’m in town.

Reviewed on May 5, 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 13 to May 14
$145 total
May 13 - May 14
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
This is a very basic clean hotel. Very busy area. Could hear a lot of road traffic. Hotel was very clean but somewhat outdated. Basic no frills but need a place to stop for the night sort of place.

Reviewed on May 4, 2026

Drury Inn & Suites Evansville East
Garner Hotel Evansville East by IHG

Garner Hotel Evansville East by IHG

3 out of 5
301 Circle Front Dr Evansville IN
Fully refundable
$78 nightly
The price is $90 total per night from May 17 to May 18
$90 total
May 17 - May 18
Total with taxes and fees
9/10 Wonderful! (154 reviews)
Smelly room. Dirty bathroom sink. Beds were clean

Reviewed on May 7, 2026

Garner Hotel Evansville East by IHG
See all 177 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 $782 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.