Oakland City Vacation Rentals

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Our top choices for Oakland City vacation rentals

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 CA $213
CA $377 total
includes taxes & fees
May 24 - May 25
Yellow Banks Log Cabin With Waterfront Views

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 CA $172
CA $218 total
includes taxes & fees
May 17 - May 18
Guest House with acreage to explore.

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 CA $206
CA $366 total
includes taxes & fees
May 18 - May 19
Yellow Banks Log Cabin with Lake Views

The LC Retreat

The LC Retreat
Lincoln City
The price is CA $248
CA $460 total
includes taxes & fees
May 18 - May 19
The LC Retreat

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 CA $172
CA $324 total
includes taxes & fees
May 18 - May 19
Yellow Banks Log Cabin With Waterfront Views

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 CA $172
CA $324 total
includes taxes & fees
May 18 - May 19
Yellow Banks Log Cabin With Waterfront Views

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 CA $402
CA $640 total
includes taxes & fees
May 18 - May 19
5 Miles from Holiday World sleeps 11+ —Family Escape

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 CA $197
CA $401 total
includes taxes & fees
May 19 - May 20
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

The Family Oasis just 6 miles from Holiday World

The Family Oasis just 6 miles from Holiday World
Gentryville
9.2 out of 10, Wonderful, (45 reviews)
"Great location to Holiday World’s "
United States
Gary S.
The price is CA $444
CA $696 total
includes taxes & fees
Jun 14 - Jun 15
The Family Oasis just 6 miles from Holiday World

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 CA $151
CA $288 total
includes taxes & fees
May 31 - Jun 1
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

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 CA $165
CA $561 total
includes taxes & fees
May 18 - May 19
Barn in the Burgh - Event Space - Sleeps 12

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 CA $126
CA $373 total
includes taxes & fees
May 25 - May 26
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

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 CA $246
CA $775 total
includes taxes & fees
May 27 - May 28
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy

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 $115
CA $258 total
includes taxes & fees
May 18 - May 19
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh

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 CA $413
CA $527 total
includes taxes & fees
Jun 1 - Jun 2
Family Friendly Lakehouse with great views!

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 CA $133
CA $289 total
includes taxes & fees
May 17 - May 18
The Chic Shack | Centrally Located 2BR/1BA Home

Trendy Two bedroom home centrally located near UE

Trendy Two bedroom home centrally located near UE
Evansville
9.4 out of 10, Exceptional, (6 reviews)
"Place was very clean. Provisions were great! We were glad to be able to do laundry. We suggest having a laundry basket and a small folding table."
United States
Carol B.
The price is CA $116
CA $244 total
includes taxes & fees
May 19 - May 20
Trendy Two bedroom home centrally located near UE

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 CA $172
CA $324 total
includes taxes & fees
May 19 - May 20
Yellow Banks Log Cabin With Waterfront Views

Modern 2BR Townhome, 1.5 Baths, Ideal for 30+ Day Stays, Workspace + Parking

Modern 2BR Townhome, 1.5 Baths, Ideal for 30+ Day Stays, Workspace + Parking
Evansville
9.2 out of 10, Wonderful, (5 reviews)
"Thank you for the great stay. We truly appreciated the space."
United States
Larry
The price is CA $108
CA $276 total
includes taxes & fees
May 19 - May 20
Modern 2BR Townhome, 1.5 Baths, Ideal for 30+ Day Stays, Workspace + Parking

Harrison Place - Located on Evansville's Eastside

Harrison Place - Located on Evansville's Eastside
Evansville
The price is CA $406
CA $734 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

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.

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?

Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy: This vacation home rental near Oakland City offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and 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.