Deals on vacations and trips to Oakland City

Save when you book Oakland City package deals

Choose two or more items and save on your trip:

Oakland City flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Garner Hotel Evansville East by IHG

Garner Hotel Evansville East by IHG

3 out of 5
Price was $819, price is now $768 per person
$768
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Evansville (EVV)
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was $1,227, price is now $1,114 per person
$1,114
per person
Dec 21 - Dec 27
found 14 hours ago
Roundtrip non-stop flight included
New Bern (EWN) to Evansville (EVV)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Holiday Inn Express & Suites Evansville North by IHG

Holiday Inn Express & Suites Evansville North by IHG

2.5 out of 5
Price was $1,134, price is now $1,062 per person
$1,062
per person
Dec 21 - Dec 27
found 14 hours ago
Roundtrip non-stop flight included
New Bern (EWN) to Evansville (EVV)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
Envi Boutique Hotel Henderson-Evansville South

Envi Boutique Hotel Henderson-Evansville South

3 out of 5
Price was $1,181, price is now $1,106 per person
$1,106
per person
Dec 21 - Dec 27
found 14 hours ago
Roundtrip non-stop flight included
New Bern (EWN) to Evansville (EVV)
This motel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, a picnic area, and dry cleaning are also on offer.
New Harmony Inn Resort and Conference Center

New Harmony Inn Resort and Conference Center

3 out of 5
Price was $1,244, price is now $1,167 per person
$1,167
per person
Dec 21 - Dec 27
found 14 hours ago
Roundtrip non-stop flight included
New Bern (EWN) to Evansville (EVV)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the sauna and perks like free self parking.

Top Oakland City hotels deals

Oakland Courtyard

Oakland Courtyard

2 out of 5
1000 W Morton St, Oakland City, Oakland City, IN
$77 nightly
The price is $86 total per night
$86 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Parking included
Free WiFi
Golf Course Views: Oakland City Retreat

Golf Course Views: Oakland City Retreat

3 out of 5
Get rates
Free WiFi in public areas is available at this cottage.
Kitchen
Free WiFi
Half-mi to Oakland City Golf Club: Sleek Apartment

Half-mi to Oakland City Golf Club: Sleek Apartment

3 out of 5
Get rates
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.
Quiet Oakland City Studio: Walk Downtown!

Quiet Oakland City Studio: Walk Downtown!

3 out of 5
Get rates
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.
Walk to Oakland City University: Modern Apartment!

Walk to Oakland City University: Modern Apartment!

3 out of 5
Get rates
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.
Kitchen
Parking included
Oakland City Apartment: Close to Dtwn

Oakland City Apartment: Close to Dtwn

3 out of 5
Get rates
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.
Don't see what you're looking for?
See all available properties in Oakland City
View all properties
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.

Popular places to visit

Oakland City University

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

Oakland City University

Frequently asked questions

How much are vacation packages to Oakland City?
Vacation packages, which include flights and hotels in Oakland City, start at just $768. Make your travel dreams a reality and begin your booking with Travelocity today.
Where can I get the best vacation package deals for Oakland City?
There are sensational Oakland City package deals to score with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties all over the world? Keep this in mind when you're ready to cross another place off your bucket list.
Why should I book my Oakland City vacation package via Travelocity?
Incredible savings, countless amazing destinations and 24/7 customer service you can rely on — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always score the best possible deal with Travelocity.
Can I save on my Oakland City car rental if I combine it with hotels and flights?
Combining your hotel, car and flight into an Oakland City vacation package is an easy way to land the best deal. Plus, having your own wheels gives you the freedom to get to all those landmarks you're itching to check out. Sitting 120 mi away from Oakland City, Indianapolis Motor Speedway is one place that should be on your to-do list. Buckle up and make a day trip of it.
Which airport is best for Oakland City?
Evansville Regional Airport (EVV), the major terminal in Oakland City, is where you'll stroll through arrivals. It's located 25 mi southwest of the center of town.
What is there to do in Oakland City?
Snap up the great photo-ops at Oakland City University, one of the most prominent attractions in Oakland City. There's a whole lot more to discover around this exciting city, so make sure you have enough time to explore some off-the-beaten-path gems.
Where should I stay when visiting Oakland City?
Many travelers opt to hit the hay at the Diplomat Motel. It's a great base for your Oakland City escape.

Photos of local treasures

Browse Oakland City vacation photos for more inspiration