Oakland City Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Oakland City vacation rentals

Smart TV

Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (65 reviews)
"The cabin was super cozy and comfortable! "
United States
Kellie J.
$145 nightly
The price is $159
May 9 - May 10
Total with taxes and fees
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.
$174 nightly
The price is $195
May 8 - May 9
Total with taxes and fees
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
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.
$217 nightly
The price is $238
May 10 - May 11
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
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.
$217 nightly
The price is $238
May 10 - May 11
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
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.
$355 nightly
The price is $389
May 10 - May 11
Total with taxes and fees
Barn in the Burgh - Event Space - Sleeps 12
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.
$251 nightly
The price is $275
May 10 - May 11
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
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.
$245 nightly
The price is $268
May 10 - May 11
Total with taxes and fees
Yellow Banks Log Cabin with Lake 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.
$248 nightly
The price is $271
May 11 - May 12
Total with taxes and fees
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Exterior

The LC Retreat

The LC Retreat
Lincoln City
$301 nightly
The price is $337
May 8 - May 9
Total with taxes and fees
The LC Retreat
Interior

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.
$289 nightly
The price is $316
May 9 - May 10
Total with taxes and fees
Tranquil Hideaway: Your Private Lakefront Retreat
2 bedrooms, iron/ironing board, WiFi, bed sheets

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.
$172 nightly
The price is $193
May 10 - May 11
Total with taxes and fees
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
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.
$260 nightly
The price is $291
May 17 - May 18
Total with taxes and fees
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
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.
$217 nightly
The price is $238
May 10 - May 11
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
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.
$186 nightly
The price is $214
May 10 - May 11
Total with taxes and fees
The Chic Shack | Centrally Located 2BR/1BA Home
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.
$217 nightly
The price is $249
May 11 - May 12
Total with taxes and fees
Mid-Century Brick Bungalow 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.
$394 nightly
The price is $441
May 10 - May 11
Total with taxes and fees
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.
$570 nightly
The price is $656
May 11 - May 12
Total with taxes and fees
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.
$324 nightly
The price is $363
May 26 - May 27
Total with taxes and fees
Family Friendly Lakehouse with great views!
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
Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
Interior

Princeton Suite 6 - QUEEN 2BR/2BA

Princeton Suite 6 - QUEEN 2BR/2BA
Princeton
2.0 out of 10, (1 review)
$179 nightly
The price is $200
May 8 - May 9
Total with taxes and fees
Princeton Suite 6 - QUEEN 2BR/2BA
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

Garner Hotel Evansville East by IHG

Garner Hotel Evansville East by IHG

6/10 Okay
"Smelly room. Dirty bathroom sink. Beds were clean"
Mary 1-night trip
Posted 2 hours ago
Garner Hotel Evansville East by IHG

Find out more about Oakland City

Everything you need to know about Oakland City vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland City vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakland City vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakland City in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakland City rentals

At Expedia, we put the best Oakland City vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.