Holiday Rentals in Oakland City

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Our top choices for Oakland City holiday rentals

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 €158
includes taxes & fees
8 Jan - 9 Jan
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
9.6 out of 10, Exceptional, (61)
"We enjoyed the property and Doug was a welcoming host. "
United States
Bess C.
The price is €143
includes taxes & fees
8 Jan - 9 Jan
Guest House with acreage to explore.

Holiday Home in Newburgh

Barn in the Burgh
10.0 out of 10, Exceptional, (13)
"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 €266
includes taxes & fees
8 Jan - 9 Jan
Barn in the Burgh
9.2 out of 10, Wonderful, (5)
"Place was very clean. Provisions were great! We were glad to be able to do laundry. We suggest having a laundry basket and a small folding table."
United States
Carol B.
The price is €143
includes taxes & fees
8 Jan - 9 Jan
Trendy Two bedroom home centrally located near UE
9.4 out of 10, Exceptional, (14)
"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 €239
includes taxes & fees
9 Jan - 10 Jan
Tranquil Hideaway: Your Private Lakefront Retreat
10.0 out of 10, Exceptional, (17)
"Great setting, good beds, and clean!"
United States
Doug W.
The price is €213
includes taxes & fees
8 Jan - 9 Jan
Yellow Banks Log Cabin With Waterfront Views
9.4 out of 10, Exceptional, (21)
"Very nice cabin very clean overall really enjoyed"
United States
Addy D.
The price is €213
includes taxes & fees
8 Jan - 9 Jan
Yellow Banks Log Cabin With Waterfront Views
9.8 out of 10, Exceptional, (34)
"Very clean quiet rustic but comfortable property."
United States
Margo B.
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
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 €149
includes taxes & fees
11 Jan - 12 Jan
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
10.0 out of 10, Exceptional, (2)
"It felt like home in this space. All the extra throw blankets to be warm and cozy. The host is very easy to work with."
United States
Meisha W.
The price is €169
includes taxes & fees
8 Jan - 9 Jan
The Chic Shack | Centrally Located 2BR/1BA Home
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 €232
includes taxes & fees
8 Jan - 9 Jan
Yellow Banks Log Cabin with Lake Views
2.0 star property
The price is €127
includes taxes & fees
11 Jan - 12 Jan
Perfect industrial studio in charming downtown Boonville
9.6 out of 10, Exceptional, (14)
"Perfect place to stay when a big space is needed"
United States
Joel Z.
The price is €336
includes taxes & fees
8 Jan - 9 Jan
5 Miles from Holiday World sleeps 11+ —Family Escape
10.0 out of 10, Exceptional, (8)
"Cute quiet lil house located around attractions for families. Well worth the money and host is always available "
United States
Madison B.
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
9.2 out of 10, Wonderful, (13)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is €213
includes taxes & fees
8 Jan - 9 Jan
Yellow Banks Log Cabin With Waterfront Views
2.0 star property
The price is €273
includes taxes & fees
12 Jan - 13 Jan
Family Friendly Lakehouse with great views!

Holiday Home in Newburgh

River View in Downtown Newburgh
8.8 out of 10, Excellent, (9)
"There was a slight ant problem but not overwhelming. "
United States
Arvin A.
The price is €499
includes taxes & fees
31 Jan - 1 Feb
River View in Downtown 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, apart-hotels, 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 €143 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?

Country Homeplace 4-bedroom Pool-HotTub pets ok Near Toyota: This holiday home rental outside of Oakland City offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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.