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Oakland City Vacation Rentals

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Our top choices for Oakland City vacation rentals

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

Princeton Suite 7 - QUEEN 1BD/1BA Apt
Princeton
The price is CA $101
CA $220 total
includes taxes & fees
Nov 15 - Nov 16
Princeton Suite 7 - QUEEN 1BD/1BA Apt

2. Princeton Suite 6 - KING 2BR/2BA

Princeton Suite 6 - KING 2BR/2BA
Princeton
2.0 out of 10, (1 review)
Princeton Suite 6 - KING 2BR/2BA

3. 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 CA $221
CA $382 total
includes taxes & fees
Nov 17 - Nov 18
Yellow Banks Log Cabin With Waterfront Views

4. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (75 reviews)
"Nice quaint place to stay. 10/10 would recommend and stay if in the area again"
United States
Chasity D.
The price is CA $204
CA $249 total
includes taxes & fees
Nov 15 - Nov 16
Guest House with acreage to explore.

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 CA $250
CA $417 total
includes taxes & fees
Nov 15 - Nov 16
Yellow Banks Log Cabin with Lake Views

6. Tranquil Hideaway: Your Private Lakefront Retreat

Tranquil Hideaway: Your Private Lakefront Retreat
Dale
9.4 out of 10, Exceptional, (14 reviews)
"The property was ideal. We have family in nearby Tennyson, and this was a perfect place to stay and visit. The host was very responsive, and the stay was pleasant and relaxing. "
United States
Jim E.
The price is CA $158
CA $410 total
includes taxes & fees
Nov 23 - Nov 24
Tranquil Hideaway: Your Private Lakefront Retreat

7. 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 CA $141
CA $265 total
includes taxes & fees
Nov 15 - Nov 16
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

8. 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 CA $138
CA $273 total
includes taxes & fees
Nov 16 - Nov 17
2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer

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

Near Deaconess & Ford Center, pet friendly, wifi
Evansville
The price is CA $131
CA $505 total
includes taxes & fees
Nov 30 - Dec 1
Near Deaconess & Ford Center, pet friendly, wifi

10. RiverStone Retreat B

RiverStone Retreat B
Newburgh
The price is CA $112
CA $228 total
includes taxes & fees
Nov 15 - Nov 16
RiverStone Retreat B

11. Cozy Cottage, 3 mins from EVV, fenced yard

Cozy Cottage, 3 mins from EVV, fenced yard
Evansville
9.8 out of 10, Exceptional, (29 reviews)
"It was a nice place for a multigenerational family to stay for a university graduation."
United States
Jennifer R.
The price is CA $464
CA $978 total
includes taxes & fees
Nov 28 - Nov 29
Cozy Cottage, 3 mins from EVV, fenced yard

12. RiverTown Retro: 1970s Retreat | 1BR Downtown Newburgh | Walk to River & Coffee

RiverTown Retro: 1970s Retreat | 1BR Downtown Newburgh | Walk to River & Coffee
Newburgh
10.0 out of 10, Exceptional, (1 review)
"Had a 4 night stay with my dog and was very happy with location and accommodations. Apartment was clean and had everything I needed. The shower was tricky to get working, I had never seen one like it before. Luckily, my daughter's boyfriend knew what to do, LOL. I will definitely try to book this place again when I'm visiting the area."
United States
Kimberli S.
The price is CA $122
CA $445 total
includes taxes & fees
Nov 15 - Nov 16
RiverTown Retro: 1970s Retreat | 1BR Downtown Newburgh | Walk to River & Coffee

13. 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

14. 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 CA $353
CA $560 total
includes taxes & fees
Nov 15 - Nov 16
5 Miles from Holiday World sleeps 11+ —Family Escape

15. Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh

Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
Newburgh
10.0 out of 10, Exceptional, (3 reviews)
"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 CA $199
CA $354 total
includes taxes & fees
Nov 20 - Nov 21
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh

16. Barn in the Burgh — Barndominium Sleeps 12 · Game Room

Barn in the Burgh — Barndominium Sleeps 12 · Game Room
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is CA $267
CA $732 total
includes taxes & fees
Dec 1 - Dec 2
Barn in the Burgh — Barndominium Sleeps 12 · Game Room

17. 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

18. 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, (15 reviews)
"Nicely decorated with top amenities. Lovely beds and linens. Worked out perfect for our family"
United States
Lori M.
The price is CA $284
CA $801 total
includes taxes & fees
Nov 17 - Nov 18
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy

19. 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 CA $144
CA $401 total
includes taxes & fees
Nov 16 - Nov 17
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

20. The Downtown Gem

The Downtown Gem
Jasper
The price is CA $270
CA $503 total
includes taxes & fees
Dec 4 - Dec 5
The Downtown Gem
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Oakland City?

Yes, you can find vacation rentals close to well known sights in Oakland City, or you can go with a more remote option if you're looking for relaxation. Oakland City is known for its restaurants and university setting.

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

Oakside Retreat – Private Getaway with Huge Yard, Firepit and Game Room: This vacation home rental near Oakland City offers a selection of games, a barbecue grill, 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 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 vacation rentals like in Oakland City?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Oakland City. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for families.