Oakland City Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Oakland City vacation rentals

Outdoor dining

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.4 out of 10, Exceptional, (21 reviews)
"Very nice cabin very clean overall really enjoyed"
United States
Addy D.
The price is ￥19,649
￥37,352 total
includes taxes & fees
May 14 - May 15
Yellow Banks Log Cabin With Waterfront Views
Property grounds

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.6 out of 10, Exceptional, (18 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
The price is ￥19,649
￥37,352 total
includes taxes & fees
May 14 - May 15
Yellow Banks Log Cabin With Waterfront Views
Smart TV

Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (66 reviews)
"The cabin was super cozy and comfortable! "
United States
Kellie J.
The price is ￥19,649
￥24,959 total
includes taxes & fees
May 14 - May 15
Guest House with acreage to explore.
Interior

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, (22 reviews)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
The price is ￥15,562
￥30,985 total
includes taxes & fees
May 14 - May 15
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Exterior

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
10.0 out of 10, Exceptional, (7 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 ￥24,364
￥43,837 total
includes taxes & fees
May 14 - May 15
Yellow Banks Log Cabin With Waterfront Views
Smart TV, books

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.8 out of 10, Exceptional, (37 reviews)
"Great stay!"
United States
Kristi M.
The price is ￥14,430
￥42,570 total
includes taxes & fees
May 21 - May 22
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Fridge, microwave, oven, stovetop

Barn in the Burgh - Event Space - Sleeps 12

Barn in the Burgh - Event Space - Sleeps 12
Newburgh
10.0 out of 10, Exceptional, (15 reviews)
"Rented for an event and everything was amazing! Will definitely try to rent again!"
United States
Sabrina W.
The price is ￥19,574
￥66,227 total
includes taxes & fees
May 18 - May 19
Barn in the Burgh - Event Space - Sleeps 12
TV

Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (19 reviews)
"It's a cute cabin and comfortable ! Shower was small and doors were a little tricky but overall good experience! Half hour away from holiday world! "
United States
Gina P.
The price is ￥23,579
￥42,171 total
includes taxes & fees
May 14 - May 15
Yellow Banks Log Cabin with Lake Views
Exterior

The LC Retreat

The LC Retreat
Lincoln City
The price is ￥28,294
￥52,992 total
includes taxes & fees
May 14 - May 15
The LC Retreat
Outdoor dining

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (13 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is ￥19,649
￥37,352 total
includes taxes & fees
May 17 - May 18
Yellow Banks Log Cabin With Waterfront Views
Fridge, microwave, oven, stovetop

Mid-Century Brick Bungalow Home

Mid-Century Brick Bungalow Home
Evansville
6.8 out of 10, (25 reviews)
"As advertised. My only feedback is that there was very little soap and we ran out in the bathroom and sink. "
United States
Lori L.
The price is ￥18,391
￥39,950 total
includes taxes & fees
May 17 - May 18
Mid-Century Brick Bungalow Home
Exterior

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Lynnville
10.0 out of 10, Exceptional, (8 reviews)
"Cute quiet lil house located around attractions for families. Well worth the money and host is always available "
United States
Madison B.
The price is ￥22,494
￥45,793 total
includes taxes & fees
May 18 - May 19
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
2 bedrooms, iron/ironing board, WiFi, bed sheets

Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh

Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
Newburgh
The price is ￥13,830
￥30,630 total
includes taxes & fees
May 17 - May 18
Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
3 bedrooms, desk, WiFi

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

The Chic Shack | Centrally Located 2BR/1BA Home
Evansville
10.0 out of 10, Exceptional, (2 reviews)
"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 ￥16,098
￥33,878 total
includes taxes & fees
May 17 - May 18
The Chic Shack | Centrally Located 2BR/1BA Home
Fridge, microwave, oven, stovetop

5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.6 out of 10, Exceptional, (17 reviews)
"Such a cute and cozy place that had everything we needed! Beds were all super comfy, and with 3 little ones with us, the game room was fantastic. Would definitely recommend!!!"
United States
Lauren M.
The price is ￥42,441
￥69,365 total
includes taxes & fees
May 14 - May 15
5 Miles from Holiday World sleeps 11+ —Family Escape
Fridge, microwave, oven, stovetop

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, (5 reviews)
"Every detail was perfect for our whole family. We couldn’t have been more comfortable. "
United States
Katie C.
The price is ￥39,140
￥103,038 total
includes taxes & fees
May 14 - May 15
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
Smart TV

Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful stay for family! Great gathering place for family and friends! Everything you would need and more!"
United States
Jill C.
The price is ￥42,836
￥53,449 total
includes taxes & fees
May 26 - May 27
Family Friendly Lakehouse with great views!
Exterior

Harrison Place - Located on Evansville's Eastside

Harrison Place - Located on Evansville's Eastside
Evansville
The price is ￥46,371
￥84,238 total
includes taxes & fees
May 21 - May 22
Harrison Place - Located on Evansville's Eastside
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

One Life Studios

One Life Studios

8/10 Good
"K"
Readle 1-night trip
Posted 1 day ago
One Life Studios

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
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  • 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 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?

Another Oasis just 6 miles from Holiday World: This vacation home rental near Oakland City has air-conditioning and laundry facilities 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.