Oakland City Holidays

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Top hotels in Oakland City

Oakland Courtyard

Oakland Courtyard

2 out of 5
1000 W Morton St, Oakland City Oakland City IN
The price is €154 per night from 20 Jul to 21 Jul
€154
20 Jul - 21 Jul
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 €109 per night from 16 Aug to 17 Aug
€109
16 Aug - 17 Aug
includes taxes & fees
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 €75 per night from 14 Aug to 15 Aug
€75
14 Aug - 15 Aug
includes taxes & fees
8/10 Very good! (764 reviews)
"Pretty nice hotel, Swimming pool and hot tub were nice, breakfast could have been better, beds were comfortable, okay TV, nice bathroom. I do really recommend this hotel!"

Reviewed on 16 Jul 2026

Jasper Inn
See all 189 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.

Stay near popular Oakland City attractions

Oakland City University

7.2/10 (47 reviews)
Enjoy the student vibe when you visit Oakland City University during your trip to Oakland City.
See properties

Frequently asked questions

How much does an Oakland City holiday package cost?
You'll find cheap prices on Expedia for your Oakland City escape. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Oakland City costs.
What are the cheapest months to go to Oakland City?
January, February and March are the best times to search for cheap Oakland City holiday packages. Choosing to travel in less busy months means you can generally find lower prices on flights and accommodation.
How many days is enough for Oakland City?
With a well-planned itinerary, you can easily tick off the main Oakland City attractions in a few days. But if you'd like to discover hidden gems or go on day tours, consider booking your Oakland City holiday for longer.
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 holiday package as soon as possible.
Is it cheaper to book an Oakland City holiday as a package?
An Expedia holiday package could land you great savings when compared to booking stays and flights individually. Better still, you can personalise 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 holiday 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.
How to plan a trip to Oakland City?

  1. Choose your travel dates: The things you'd like to do in Oakland City and your preferred season can help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and meals to experiences and flights. Your hotel will probably be the biggest expense during your trip to Oakland City.
  3. Work out your trip length: Consider how long you want to spend discovering Oakland City. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick an Oakland City holiday package that brings all your bookings together.

Explore a world of travel with Expedia

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