Book Exclusive Oakland City Vacation Packages

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Oakland City flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
PT6 INN

PT6 INN

2.5 out of 5
Price was CA $871, price is now CA $846 per person
CA $846
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Evansville (EVV)
Stay at this motel in Evansville. Enjoy free WiFi, free parking, and a casino. Popular attractions Ford Center and Homestead Park are located nearby.
Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was CA $977, price is now CA $935 per person
CA $935
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Evansville (EVV)
Book a stay at this business-friendly hotel in Evansville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Ford Center and Gattitown Evansville Indiana Pizza & Family Entertainment Center are located nearby.
Howard Johnson by Wyndham Evansville East

Howard Johnson by Wyndham Evansville East

2.5 out of 5
Price was CA $888, price is now CA $870 per person
CA $870
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Evansville (EVV)
Book a stay at this business-friendly hotel in Evansville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ford Center and Eastland Mall are located nearby.
Sleep Inn Henderson-Evansville South

Sleep Inn Henderson-Evansville South

2.5 out of 5
Price was CA $939, price is now CA $920 per person
CA $920
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Evansville (EVV)
Book a stay at this business-friendly hotel in Henderson. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Atkinson Park and Scenic Lake are located nearby.
Envi Boutique Hotel Henderson-Evansville South

Envi Boutique Hotel Henderson-Evansville South

3 out of 5
Price was CA $928, price is now CA $910 per person
CA $910
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Evansville (EVV)
Book a stay at this business-friendly motel in Henderson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Atkinson Park and Henderson Municipal Golf Course are located nearby.

Top Oakland City hotels deals

Oakland Courtyard

Oakland Courtyard

2 out of 5
1000 W Morton St, Oakland City Oakland City IN
The price is CA $214 per night
CA $214
CA $240 total
Jul 27 - Jul 28
includes taxes & fees
Stay at this hotel in Oakland City. Enjoy free WiFi, free parking, and a 24-hour front desk.
Parking included
Free WiFi
Santas Lodge and Resort

Santas Lodge and Resort

2.5 out of 5
91 W CHRISTMAS BLVD Santa Claus IN
Free cancellation
Reserve now, pay when you stay
The price is CA $142 per night
CA $142
CA $159 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this hotel in Santa Claus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Holiday World and Splashin' Safari and Frosty's Fun Center are located nearby.
Pool
Breakfast included
Jasper Inn

Jasper Inn

2.5 out of 5
951 Wernsing Road Jasper IN
Free cancellation
Reserve now, pay when you stay
The price is CA $115 per night
CA $115
CA $129 total
Aug 9 - Aug 10
includes taxes & fees
Book a stay at this business-friendly hotel in Jasper. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Jasper Youth Sports Complex and Jasper City Mill are located nearby.
Pool
Hot tub
Comfort Inn Ferdinand

Comfort Inn Ferdinand

2.5 out of 5
123 Scenic Hills Court Ferdinand IN
Free cancellation
The price is CA $130 per night
CA $130
CA $146 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this business-friendly hotel in Ferdinand. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions 5th Street Park and Monastery Immaculate conception are located nearby.
Pool
Breakfast included
La Quinta Inn & Suites by Wyndham Evansville

La Quinta Inn & Suites by Wyndham Evansville

3 out of 5
8015 East Division Street Evansville IN
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $136 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Evansville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Gattitown Evansville Indiana Pizza & Family Entertainment Center and Eastland Mall are located nearby.
Pool
Breakfast included
Drury Inn & Suites Evansville East

Drury Inn & Suites Evansville East

3 out of 5
100 Cross Pointe Blvd Evansville IN
Free cancellation
Reserve now, pay when you stay
The price is CA $164 per night
CA $164
CA $189 total
Jul 23 - Jul 24
includes taxes & fees
Book a stay at this business-friendly hotel in Evansville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ford Center and Gattitown Evansville Indiana Pizza & Family Entertainment Center are located nearby.
Pool
Hot tub
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Stay near popular Oakland City attractions

Oakland City University

7.2/10 (47 reviews)
Explore the campus of Oakland City University, during your trip to Oakland City.
See properties

Oakland City Vacations

If you missed the day your geography teacher told your class where Oakland City is situated, there's no need to fret. With a helping hand from us, you'll find it on your map in no time!

Oakland City lies 14 miles (23 kilometers) east of Princeton. It is also 17 miles (27 kilometers) north of Boonville.

Enjoy meeting the locals while you're on vacation? This area of Indiana has a population of around 2,000 residents.

Places to visit in Oakland City

It has often been said that the pen is mightier than the sword, and Oakland City University is one of the best examples of this. Have a look around the campus and discover the triumphs of its greatest thinkers. Also, if you really want to experience the Indiana region like the locals do, make sure you go hiking. Not just a popular activity around these parts, it's also terrific fun!

Where do you fly into for Oakland City?

Put on your headphones and pick an in-flight movie. In no time at all, you'll be landing at Evansville Regional Airport (EVV). It's approximately 20 miles (32 kilometers) to the southwest from the heart of Oakland City.

Frequently asked questions

How much are vacation packages to Oakland City?
Vacation packages, which include flights and hotels in Oakland City, start at just CA $846. 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 193 kilometers 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 40 kilometers 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

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