Oakland City Holiday Rentals

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Holiday Rentals in Oakland City

Property grounds
Rustic Guest House with acreage to explore.
9.6 out of 10, Exceptional, (33)
"Doug was awesome! The property had probably the best bed we have slept in. He was thoughtful and had some protectors for the couches knowing we had a couple dogs with us. It was nice and quiet out at his place though we didn't get to explore because of family obligations. My car decided to die on us and he was so kind offering help and not mad about the circumstance of essentially checking out a hour late due to having to run into town and back for a new battery. We greatly appreciate his...
The price is NZ$265
per night
28 May - 29 May
Rustic Guest House with acreage to explore.
Property grounds
The Family Oasis just 6 miles from Holiday World
8.8 out of 10, Excellent, (18)
"Excellent location, quiet, clean with nice thoughtful touches to make a welcoming stay. Perfect place to have a weekend getaway."
The price is NZ$758
per night
8 Jun - 9 Jun
The Family Oasis just 6 miles from Holiday World
Aerial view
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
10.0 out of 10, Exceptional, (1)
"My family and I booked at the last minute so we could go view the Solar Eclipse. The process of booking, checking in and checking out was a breeze. Jodey was very responsive and extremely helpful in making our stay very enjoyable. We would highly recommend a stay here, and we hope to return for a Christmas visit to Santa Claus."
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
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Fridge, microwave, oven, stovetop
Cozy Bungalow in a nice friendly neighborhood
9.8 out of 10, Exceptional, (50)
"This was a the perfect fit for a short stay in Evansville. The neighborhood was quiet, and I felt very safe staying there. It is just a short 7-minute drive to downtown. The owners were very responsive and answered all of my questions."
Cozy Bungalow in a nice friendly neighborhood
Exterior
Another Oasis just 6 miles from Holiday World
9.0 out of 10, Wonderful, (4)
"We brought our son and his wife and kids to our holiday world mini vacation. There was plenty of space for all of us and lots of space for the kids to run and play. They even had games for the kids. The place was exactly as described. The host was very easy to communicate with and promp with responses. We will definitely plan to stay there again!"
The price is NZ$783
per night
14 Jun - 15 Jun
Another Oasis just 6 miles from Holiday World
Smart TV
Yellow Banks Log Cabin With Waterfront Views
9.6 out of 10, Exceptional, (5)
"Everything was great"
The price is NZ$461
per night
27 May - 28 May
Yellow Banks Log Cabin With Waterfront Views
Private kitchen
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
10.0 out of 10, Exceptional, (1)
"A great fully finished basement with ample room for a group. Wonderful location to stay to enjoy all that Dubois County has to offer."
The price is NZ$348
per night
27 May - 28 May
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Fridge, microwave, oven, stovetop
X Marks the Spot(Blue)1.5 miles from Holiday World
10.0 out of 10, Exceptional, (1)
"Very nice and clean."
X Marks the Spot(Blue)1.5 miles from Holiday World
Fridge, microwave, oven, stovetop
X Marks the Spot (Purple)
X Marks the Spot (Purple)
Fridge, microwave, oven, stovetop
Comfort and Charm Highly Recommended
9.4 out of 10, Exceptional, (8)
"Great place to host family for graduation celebration."
Comfort and Charm Highly Recommended
View from property
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
9.8 out of 10, Exceptional, (19)
"nice and quiet"
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
10.0 out of 10, Exceptional, (4)
"Easy and quick stay Easy of booking on short notice. Very clean and well maintained property. Comfortable bed. As described Thank goodness!!!"
The price is NZ$412
per night
27 May - 28 May
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
Property grounds
Yellow Banks Log Cabin With Waterfront Views
9.8 out of 10, Exceptional, (6)
"My family loved the cabin my oldest daughter is even thinking of booking it in the near future for a little get away. The owner is amazing as I messed up booking days and they went above and beyond to assure we had a place to stay and remained in communication with us until everything was right. All around a great peaceful place we enjoyed it"
The price is NZ$461
per night
27 May - 28 May
Yellow Banks Log Cabin With Waterfront Views
Private kitchen
Sweet Spot in the City
The price is NZ$573
per night
27 May - 28 May
Sweet Spot in the City
Interior
Indiana Studio 6 Miles to Downtown Huntingburg
9.4 out of 10, Exceptional, (3)
"We loved our long weekend vacation. The location was fantastic with easy access to holiday world being a short 20 minute drive. Amenities here were awesome with the hot tub being our favorite. The owner was great to talk with, and had some great recommendations for things to check out in the area. Looking forward to coming back."
Indiana Studio 6 Miles to Downtown Huntingburg
Interior
Yellow Banks Log Cabin With Waterfront Views
10.0 out of 10, Exceptional, (3)
"Contact with property manager was awesome, and super easy. He sent me recommendations for nearby food, and even found somewhere i could but fishbait at. The cabin was perfect for my family(2 adults, 5 year old and a 9 year old). My only suggestion is to add a light in the shower, as it get pretty dark inside there. But wonderful place to stay, and wonderful people for Contact. Will def stay again!"
The price is NZ$461
per night
27 May - 28 May
Yellow Banks Log Cabin With Waterfront Views
Exterior
Chestnut Street Retreat
10.0 out of 10, Exceptional, (26)
"Property was great. Quiet area, clean and comfortable. Would love to come and do it again. A grill outside would be nice."
Chestnut Street Retreat
Fridge, microwave, oven, stovetop
Fenced-In Yard on the East Side
10.0 out of 10, Exceptional, (2)
"Great place to stay, Very clean and comfortable home, Nice quite neighborhood."
The price is NZ$471
per night
3 Jun - 4 Jun
Fenced-In Yard on the East Side
Smart TV
New Construction | New Furnishings | Luxury Unit
10.0 out of 10, Exceptional, (1)
"This unit is absolutely spotless and comfortable. Keith was an incredibly gracious host, and the whole experience was pleasant and easy. I highly recommend this property and host to anyone looking for a comfortable place to stay in Evansville."
The price is NZ$647
per night
27 May - 28 May
New Construction | New Furnishings | Luxury Unit
Fridge, microwave, oven, stovetop
X Marks the Spot (Green)
X Marks the Spot (Green)
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See all available 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.

Other types of properties in Oakland City you may be interested in

Lobby
Baymont by Wyndham Evansville East
2.5 star property
8.0 out of 10, Very good, (1007)
"Easy to check in."
The price is NZ$134
per night
27 May - 28 May
Baymont by Wyndham Evansville East
Premium bedding, desk, iron/ironing board, free cots/infant beds
La Quinta Inn & Suites by Wyndham Evansville
2.5 star property
8.4 out of 10, Very good, (1007)
"The staff was wonderful. They were efficient and easy to talk with. I was very impressed with the features. Nice variety of breakfast items, very clean room and overall property, great shower pressure, and wonderful bathroom lighting. The bed and pillow were some of the most comfortable I have ever had. Left with very positive feelings and a plan to stay there the next time I am in Evansville."
The price is NZ$142
per night
28 May - 29 May
La Quinta Inn & Suites by Wyndham Evansville
Lobby
Drury Inn & Suites Evansville East
3.0 star property
9.2 out of 10, Wonderful, (1003)
"We always choose Drury Inn clean confortabke hosipitality outstandingly "
The price is NZ$194
per night
2 Jun - 3 Jun
Drury Inn & Suites Evansville East
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakland City holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakland City. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oakland City. Seeing all the best attractions is bound to make you fall in love with Oakland City. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oakland City short-term rentals, that won’t be hard to do.

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?

The Family Oasis just 6 miles from Holiday World: This holiday home rental outside of Oakland City is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.

Recent reviews of Oakland City properties
Expedia verified reviews