Oakland City Holiday Rentals

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Our top choices for Oakland City holiday rentals

10.0 out of 10, Exceptional, (7)
"This was a quiet, clean, and convenient little cabin close to Holiday World which is what we stayed for. "
United States
Ashley J.
The price is NZ$479
includes taxes & fees
23 Dec - 24 Dec
Yellow Banks Log Cabin With Waterfront Views
9.6 out of 10, Exceptional, (61)
"We enjoyed the property and Doug was a welcoming host. "
United States
Bess C.
The price is NZ$276
includes taxes & fees
27 Dec - 28 Dec
Guest House with acreage to explore.
9.8 out of 10, Exceptional, (20)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
The price is NZ$340
includes taxes & fees
26 Dec - 27 Dec
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
9.8 out of 10, Exceptional, (34)
"Very clean quiet rustic but comfortable property."
United States
Margo B.
The price is NZ$471
includes taxes & fees
23 Dec - 24 Dec
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
8.8 out of 10, Excellent, (19)
"The cabin was a cozy place to stay and close enough to holiday world without the headache of keeping my younger kids silent like I would have if we stayed in a hotel! Very clean and organized! "
United States
Ashley J.
The price is NZ$449
includes taxes & fees
23 Dec - 24 Dec
Yellow Banks Log Cabin with Lake Views
10.0 out of 10, Exceptional, (17)
"Great setting, good beds, and clean!"
United States
Doug W.
The price is NZ$413
includes taxes & fees
28 Dec - 29 Dec
Yellow Banks Log Cabin With Waterfront Views
9.6 out of 10, Exceptional, (20)
"Very nice cabin very clean overall really enjoyed"
United States
Addy D.
The price is NZ$413
includes taxes & fees
28 Dec - 29 Dec
Yellow Banks Log Cabin With Waterfront Views
10.0 out of 10, Exceptional, (2)
"Very nice place! The outdoor lighting is really cool with the trees lit up and the house numbers lit up, as well. Only a 5 minute drive to the shops and restaurants on the river. "
United States
stephanie b.
The price is NZ$296
includes taxes & fees
28 Dec - 29 Dec
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
9.4 out of 10, Exceptional, (13)
"This property is amazing! We loved the privacy and peacefulness. The house is great and we will definitely be coming back!"
United States
Natalie S.
The price is NZ$459
includes taxes & fees
24 Dec - 25 Dec
Tranquil Hideaway: Your Private Lakefront Retreat
9.4 out of 10, Exceptional, (12)
"Perfect place to stay when a big space is needed"
United States
Joel Z.
The price is NZ$667
includes taxes & fees
28 Dec - 29 Dec
5 Miles from Holiday World sleeps 11+ —Family Escape
7.8 out of 10, Good, (7)
"We arrived around 8:30pm to find sleeping arrangements for 4 adults. The couch is about 4' long. We chose this place because it is listed as sleeping 5, but it's not. We woke up in the morning to shower and found a pitiful excuse of a shower. It dripped water. I took a video but unfortunately there is nowhere to upload it. It was sad. As if this wasn't enough, the kitchen utensils on the stove were covered in dried food and the vanity in the shower was not secure and fell off and landed on my...
United States
Sam S.
Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything

Holiday Home in Newburgh

Barn in the Burgh
10.0 out of 10, Exceptional, (11)
"Beautiful warm cozy place. We stayed due to a funeral and it is the perfect place wind down and relax. Planning to come back again! "
United States
Rebecca P.
The price is NZ$622
includes taxes & fees
12 Jan - 13 Jan 2026
Barn in the Burgh

Holiday Home in Evansville

Mid-Century Brick Bungalow Home
6.6 out of 10, (20)
"Close to everything we wanted to do."
United States
Mona
The price is NZ$419
includes taxes & fees
23 Dec - 24 Dec
Mid-Century Brick Bungalow Home
The price is NZ$731
includes taxes & fees
29 Dec - 30 Dec
Fall Bliss: Charming 3BR Home with Sauna & Hot Tub
9.2 out of 10, Wonderful, (13)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is NZ$413
includes taxes & fees
23 Dec - 24 Dec
Yellow Banks Log Cabin With Waterfront Views
2.0 star property
The price is NZ$586
includes taxes & fees
28 Dec - 29 Dec
Family Friendly Lakehouse with great views!
2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer
Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
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.
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Top Oakland City Hotel Reviews

Find out more about Oakland City

Everything you need to know about Oakland City holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland City holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland City holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland City holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland City. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland City holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland City holiday rentals we have selected for you start as low as NZ$276 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland City rentals

At Expedia, we put the best Oakland City holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland City holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Oakland City?

Yes, there are holiday rentals close to the most popular sights in Oakland City, or you can select a more secluded option if you're looking for a relaxing stay. Oakland City is known for its restaurants and university setting.

What are some of the best holiday rentals that Oakland City has to offer?

Tranquil Hideaway: Your Private Lakefront Retreat: This holiday home rental outside of Oakland City is located on the waterfront, and has a fireplace, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Oakland City?

Visit the sights while you're exploring the area such as Oakland City University and Wabash Erie Canal Park.

What are holiday rentals like in Oakland City?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland City. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.