Oakland City Vacation Rentals

Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Oakland City vacation rentals

Smart TV

Cabin in Tennyson

Guest House with acreage to explore.
9.6 out of 10, Exceptional, (61 reviews)
"The cabin was super cozy and comfortable! "
United States
Kellie J.
$145 nightly
The price is $159
Mar 17 - Mar 18
Total with taxes and fees
Guest House with acreage to explore.
Outdoor dining

Cabin in Dale

Yellow Banks Log Cabin With Waterfront Views
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
Mar 17 - Mar 18
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Smart TV, books

Vacation Home in Newburgh

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
9.8 out of 10, Exceptional, (34 reviews)
"Great stay!"
United States
Kristi M.
$248 nightly
The price is $271
Mar 17 - Mar 18
Total with taxes and fees
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
TV

Cabin in Dale

Yellow Banks Log Cabin with Lake Views
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.
$246 nightly
The price is $269
Mar 17 - Mar 18
Total with taxes and fees
Yellow Banks Log Cabin with Lake Views
Interior

Vacation Home in Huntingburg

Spacious 1450 sf 2 BR Private Suite w/Dog Fe
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
Mar 17 - Mar 18
Total with taxes and fees
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Fridge, microwave, oven, stovetop

Vacation Home in Newburgh

Barn in the Burgh
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful warm cozy place. We stayed due to a funeral and it is the perfect place wind down and relax. Planning to come back again! "
United States
Rebecca P.
$362 nightly
The price is $397
Mar 17 - Mar 18
Total with taxes and fees
Barn in the Burgh
Exterior

Cabin in Dale

Yellow Banks Log Cabin With Waterfront Views
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.
$252 nightly
The price is $276
Apr 1 - Apr 2
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Property grounds

Cabin in Dale

Yellow Banks Log Cabin With Waterfront Views
9.6 out of 10, Exceptional, (18 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
$214 nightly
The price is $234
Apr 1 - Apr 2
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
2 bedrooms, iron/ironing board, WiFi, bed sheets

Vacation Home in Evansville

2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer
$160 nightly
The price is $184
Mar 17 - Mar 18
Total with taxes and fees
2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer
Exterior

Vacation Home in Lynnville

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
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.
$261 nightly
The price is $292
Mar 17 - Mar 18
Total with taxes and fees
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Outdoor dining

Cabin in Dale

Yellow Banks Log Cabin With Waterfront Views
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
Mar 17 - Mar 18
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Interior

Vacation Home in Dale

Tranquil Hideaway: Your Private Lakefront Retreat
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.
$256 nightly
The price is $280
Mar 31 - Apr 1
Total with taxes and fees
Tranquil Hideaway: Your Private Lakefront Retreat
Fridge, microwave, oven, stovetop

Vacation Home in Evansville

Mid-Century Brick Bungalow Home
7.0 out of 10, Good, (23 reviews)
"Perfect for a weekend get away."
United States
Ja-Vanman
$207 nightly
The price is $238
Apr 14 - Apr 15
Total with taxes and fees
Mid-Century Brick Bungalow Home
Exterior

Cabin in Lincoln City

The LC Retreat
$200 nightly
The price is $224
Mar 17 - Mar 18
Total with taxes and fees
The LC Retreat
Fridge, microwave, oven, stovetop

Vacation Home in Dale

5 Miles from Holiday World sleeps 11+ —Family Escape
9.6 out of 10, Exceptional, (16 reviews)
"Perfect place to stay when a big space is needed"
United States
Joel Z.
$343 nightly
The price is $384
Mar 24 - Mar 25
Total with taxes and fees
5 Miles from Holiday World sleeps 11+ —Family Escape
Smart TV

Vacation Home in Jasper

Family Friendly Lakehouse with great views!
10.0 out of 10, Exceptional, (1 review)
$279 nightly
The price is $312
Mar 19 - Mar 20
Total with taxes and fees
Family Friendly Lakehouse with great views!
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Vacation Home in Evansville

Cozy Corner / 2BR/1BA EVV Apartment
2.0 out of 10, (1 review)
"Property located in cul-de-sac. All duplexes that appeared to be unkept govt. subsidized housing. Duplex next to property gas windows boarded. Attached duplex had numerous vehicles in yard with older boy laying across the car. Step up to porch approx 16" off ground with no handrail. Home had uneven floors. Freezer with approx 4" frost. Called host, called VRBO letting them know we were not staying. No resolution has been made. Host refuses any contact concerning reimbursement, partial or full....
United States
Victoria S.
$168 nightly
The price is $193
Mar 18 - Mar 19
Total with taxes and fees
Cozy Corner / 2BR/1BA EVV Apartment
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

2/10 Terrible
"did not even stay here … NOT at all as “describe” online. pulled in the parking lot && left. VERY DISAPPOINTING !! felt very uncomfortable. "
Melissa 2-night trip
Posted 3 hours ago
One Life Studios

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 $234 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?

Cozy Bungalow in a nice friendly neighborhood: This vacation home rental near Oakland City offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.