Oakland City Vacation Packages

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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.

Top Oakland City Vacation Deals

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)
4.6/10 (112 reviews)
the room was disgustingly dirty, walls dirty bathroom had someones used soap with hair, cobwebs everywhere the staff wasnt even there when we arrived i didnt think we would be able to get in our room! had to call support multiple times. definitely getting what u pay for here. and the room smelled like cigarettes dirty sheets BUGS gnats spiders its a hell no for me

Reviewed on Jun 28, 2026

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)
8.6/10 Excellent! (549 reviews)
We had an excellent stay! Property is very clean and management and staff are hospitable and accommodating. I would definitely recommend a stay here while in Evansville IN!

Reviewed on Jul 11, 2026

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)
8/10 Very good! (1,011 reviews)
Was a stop on our roadtrip. Good price for a 1 night stay.

Reviewed on Jul 16, 2026

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)
8/10 Very good! (470 reviews)
Very comfortable beds. You can tell this used to be a bit of a rougher property and there's small signs that things have been patched over a bit, but overall the room was what I would consider above average. The breakfast area was very well maintained and staffed and was definitely one of the nicer ones I have seen for this price level of hotel. (Regular AND chocolate waffle batter!) Overall, very happy with the value we got for the price paid.

Reviewed on Jul 17, 2026

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)
7.8/10 Good! (318 reviews)
Bad

Reviewed on Jul 3, 2026

Ready to book your vacation to Oakland City?

 

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Oakland City Hotel 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 from Jul 26 to Jul 27
CA $214
CA $240 total
Jul 26 - Jul 27
includes taxes & 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
The price is CA $138 per night from Aug 19 to Aug 20
CA $138
CA $155 total
Aug 19 - Aug 20
includes taxes & fees
8/10 Very good! (366 reviews)
"The staff was very friendly and helpful nicest motel I’ve ever stayed at. We stayed 4 nights it was great. Breakfast was good. Except they had the same thing all week. Maybe guests don’t stay as long as we did. But we still enjoyed the stay"

Reviewed on Jul 18, 2026

Santas Lodge and Resort
Jasper Inn

Jasper Inn

2.5 out of 5
951 Wernsing Road Jasper IN
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Aug 14 to Aug 15
CA $107
CA $120 total
Aug 14 - Aug 15
includes taxes & fees
Jasper Inn
See all 190 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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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

Frequently asked questions

How much does an Oakland City vacation package cost?
You can grab a vacation package to this top destination from CA $846 on Expedia. But how much your vacation to Oakland City costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Oakland City?
If you're looking to snag a cheap Oakland City vacation package, consider travelling in January, February and March. You'll typically find lower rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Oakland City?
The ideal duration for your Oakland City vacation depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to tick off all the leading sights and discover some hidden treasures along the way.
How to find the best Oakland City package deals?
Finding a cheap Oakland City package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Oakland City package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland City vacation as a package?
You can enjoy significant savings on your next Oakland City retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Oakland City?
If you have your Oakland City travel dates confirmed, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Oakland City?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to visit Oakland City.
  2. Plan your budget wisely: As well as the cost of your hotel, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected costs that could arise during your trip to Oakland City.
  3. Decide how long to go away for: Now that you're up to speed on Oakland City, you can work out the perfect length of your vacation. Put together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, book the right Oakland City vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.