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Oakland City Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Oakland City holiday rentals

A bedroom with a wooden wall panel, a bed with white bedding, and a small shelf with decorative items.

1. Princeton Suite 7 - QUEEN 1BD/1BA Apt

Princeton Suite 7 - QUEEN 1BD/1BA Apt
Princeton
The price is HK$545
HK$1,269 total
includes taxes & fees
1 Nov - 2 Nov
Princeton Suite 7 - QUEEN 1BD/1BA Apt
A wooden cabin with a porch, a picnic table, and a fire pit.

2. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (37 reviews)
"Very happy with our stay here. The cabin was clean, the beds were comfortable, and the owners were very easy to communicate with. We would definitely stay here again."
United States
Cyndi L.
The price is HK$980
HK$1,906 total
includes taxes & fees
28 Oct - 29 Oct
Yellow Banks Log Cabin With Waterfront Views
A wooden gazebo with a gravel path leading to a pond, surrounded by trees and a grassy area.

3. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (25 reviews)
"Great location,very clean and cozy!"
United States
Briley E.
The price is HK$1,176
HK$2,161 total
includes taxes & fees
28 Oct - 29 Oct
Yellow Banks Log Cabin With Waterfront Views
A rustic wooden building with a covered porch and a picnic table.

4. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.8 out of 10, Exceptional, (8 reviews)
"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 HK$1,216
HK$2,213 total
includes taxes & fees
28 Oct - 29 Oct
Yellow Banks Log Cabin With Waterfront Views
A cozy cabin interior with a sofa, dining table, and chairs.

5. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (29 reviews)
"A nice little cabin for our trip to holiday world."
United States
Brandon R.
The price is HK$1,372
HK$2,415 total
includes taxes & fees
1 Nov - 2 Nov
Yellow Banks Log Cabin with Lake Views
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

6. Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Huntingburg
9.8 out of 10, Exceptional, (30 reviews)
"Me and my family stayed while visiting holiday world and we highly recommend. Prices was affordable and the host was great."
United States
James B.
The price is HK$776
HK$1,528 total
includes taxes & fees
28 Oct - 29 Oct
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A wooden interior with a television, wooden cabinets, and a plant.

7. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (74 reviews)
"Nice quaint place to stay. 10/10 would recommend and stay if in the area again"
United States
Chasity D.
The price is HK$1,121
HK$1,441 total
includes taxes & fees
29 Oct - 30 Oct
Guest House with acreage to explore.
A wooden cabin with a covered porch, a picnic table, and a view of a lake.

8. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.0 out of 10, Wonderful, (18 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is HK$1,176
HK$2,161 total
includes taxes & fees
28 Oct - 29 Oct
Yellow Banks Log Cabin With Waterfront Views
A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

9. Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space

Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is HK$996
HK$3,364 total
includes taxes & fees
28 Oct - 29 Oct
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

10. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
10.0 out of 10, Exceptional, (2 reviews)
"We had an excellent stay! Place was nice and homey, well decorated and perfectly clean! Host was on top of making sure we had everything we needed. Would definitely recommend for anyone wanting to stay close to Holiday World or Lincoln State Park!"
United States
Jennifer C.
The price is HK$863
HK$3,162 total
includes taxes & fees
28 Oct - 29 Oct
The Cowboys Slumber' 2 Mi to Lincoln State Park
A modern bedroom with a large bed, a bedside table with a lamp, and a window with curtains.

11. 2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer

2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer
Evansville
2.0 out of 10, (1 review)
"This property is not what you see in the pictures. It's shabby and rough inside, including missing molding, patched walls and scuffed up furniture. We walked in and there were flies all over the kitchen and dead on the counter. It probably was a temporary problem, but not something you want to walk in on when you're paying for the space. The beds were made, but not sure that the house had been cleaned recently based on the kitchen. The outside of the house is also rough. Parking on the...
United States
Heather M.
The price is HK$701
HK$1,573 total
includes taxes & fees
28 Oct - 29 Oct
2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer
A modern living room with a sofa, ottoman, and a coffee table.

12. Near Deaconess & Ford Center, pet friendly, wifi

Near Deaconess & Ford Center, pet friendly, wifi
Evansville
The price is HK$833
HK$3,077 total
includes taxes & fees
2 Nov - 3 Nov
Near Deaconess & Ford Center, pet friendly, wifi
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

13. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
3.0 star property
Gentryville
The price is HK$1,176
HK$3,091 total
includes taxes & fees
28 Oct - 29 Oct
The Cowboys Slumber' 2 Mi to Lincoln State Park
A modern hotel room with a large flat-screen TV, a dining area with a chandelier, and a cozy seating arrangement.

14. The Chic Shack | Centrally Located 2BR/1BA Home

The Chic Shack | Centrally Located 2BR/1BA Home
Evansville
10.0 out of 10, Exceptional, (3 reviews)
"Only stayed one night during the week, but the neighborhood was quiet, the location was convenient for my business and the house had everything I needed. Slept very well and would book this one again."
United States
Jake T.
The Chic Shack | Centrally Located 2BR/1BA Home
A modern living room with a white sofa, a black leather chair, a wooden coffee table, and a dining area in the background.

15. Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything

Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything
Evansville
7.8 out of 10, Good, (7 reviews)
"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
A neatly made bed with rolled towels, a patterned throw, and a yellow pillow.

16. RiverStone Retreat A

RiverStone Retreat A
Newburgh
8.8 out of 10, Excellent, (3 reviews)
"The host was very prompt on his responses. The apartment was very well maintained and clean. There are only a couple of glasses so that would be the only thing I'd change. Overall great experience. Me and my partner want to stay next time we get a VRBO 10/10"
United States
Unspecified U.
The price is HK$602
HK$1,307 total
includes taxes & fees
28 Oct - 29 Oct
RiverStone Retreat A
A compact kitchen with wooden cabinets, a stainless steel refrigerator, an oven, a microwave, a sink, and a kettle. There is a dining table with chairs.

17. 5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.8 out of 10, Exceptional, (35 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is HK$1,941
HK$3,228 total
includes taxes & fees
8 Nov - 9 Nov
5 Miles from Holiday World sleeps 11+ —Family Escape
A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

18. Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.6 out of 10, Exceptional, (45 reviews)
"Great location, quiet but still close to shopping and restaurants. Use of the garage was a plus as it was raining the day we were packing up to leave."
United States
chris g.
The price is HK$791
HK$2,308 total
includes taxes & fees
29 Oct - 30 Oct
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

19. Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy

Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
Evansville
10.0 out of 10, Exceptional, (14 reviews)
"Nicely decorated with top amenities. Lovely beds and linens. Worked out perfect for our family"
United States
Lori M.
The price is HK$2,031
HK$5,249 total
includes taxes & fees
28 Oct - 29 Oct
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
A living room with a TV, sofa, coffee table, and a dining area with a chair and table.

20. Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!

Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
Evansville
The price is HK$565
HK$1,650 total
includes taxes & fees
17 Nov - 18 Nov
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
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

Comfort Inn Evansville East

Comfort Inn Evansville East

8/10 Good
"Convenient location"
Brian 3-night trip
Posted less than an hour ago
Comfort Inn Evansville East

Find out more about Oakland City

Search for holiday rentals in Oakland City on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland City using one of the methods below:

  • View our selection of featured holiday rentals in Oakland City
  • Use the map to find apartments and other holiday homes in the Oakland City neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland City while they last

Look no further and take a look at our great range of rental properties in Oakland City!

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?

Oakside Retreat – Private Getaway with Huge Yard, Firepit and Game Room: This holiday home rental outside of Oakland City offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. 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 such as Oakland City University while you're exploring the area.

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.