Oakland City Vacation Rentals

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Vacation Rentals in Oakland City

< 1 Mi to Oakland City University: Quiet Studio

< 1 Mi to Oakland City University: Quiet Studio

Golf Course Views: Oakland City Retreat

Golf Course Views: Oakland City Retreat

Walk to OCU, Golf: Updated Oakland City Studio!

Walk to OCU, Golf: Updated Oakland City Studio!

Half-Mi to Oakland City Golf Club: Sleek Apartment

Half-Mi to Oakland City Golf Club: Sleek Apartment

Oakland City Apartment: Close to Dtwn

Oakland City Apartment: Close to Dtwn

Golf, Shop, Tour & More: Oakland City Apartment

Golf, Shop, Tour & More: Oakland City Apartment

Walk to Oakland City University: Modern Apartment!

Walk to Oakland City University: Modern Apartment!

< 1 Mi to Oakland City University: Cozy Apartment

< 1 Mi to Oakland City University: Cozy Apartment

Golf Course Views: Oakland City Retreat

3.0 star property
Golf Course Views: Oakland City Retreat

The Potter Cottage -A great family getaway 3 miles from Holiday World

10.0 out of 10, Exceptional, (160)
"The house was very clean on arrival and was nicely decorated! It was the perfect spot for a weekend stay. We even made the mistake of taking the Bluetooth speaker thinking our friend left it behind and the host was very understanding and we were able to get it back to them! "
The Potter Cottage -A great family getaway 3 miles from Holiday World

Cozy Bungalow in a nice friendly neighborhood

9.8 out of 10, Exceptional, (59)
"My husband and I stayed in the Bungalow for a month. Kevin was very pleasant. When severe weather hit he was helpful in making sure we had ice melt and checked on our other needs. The house is very comfortable. The kitchen is fully equipped. My only suggested improvements would be to have another reading lamp in the living room and blinds on the kitchen door and window. We highly recommend this house."
Cozy Bungalow in a nice friendly neighborhood

Enchanting historical home with River View

9.8 out of 10, Exceptional, (17)
"This home was on a very quiet street. The interior has been beautifully updated. The beds were, for the most part, comfortable. Plenty of blankets and pillows were provided. The kitchen was stocked very well for our needs. The owner reponded with any questions I had very promptly and check out was so easy! We were in town for softball so we were in and out of the house often and there was plenty of room for 3 adults and 4 kids (including an infant). Really enjoyed the comfort of this home!"
The price is CA $198
CA $468 total
includes taxes & fees
Mar 23 - Mar 24
Enchanting historical home with River View

Chestnut Street Retreat

10.0 out of 10, Exceptional, (33)
"My family and I came down for Holiday World. Perfect homey place to relax before and after! Would totally return!"
Chestnut Street Retreat

Guest House with acreage to explore.

9.6 out of 10, Exceptional, (49)
"We stayed at this cabin for a full week and had an amazing time. It was tucked away and on a beautiful piece of property. We drove to town (15-30 min depending on where we went) for some good restaurants and sightseeing. We would stay again in a heartbeat. Mr. Doug was a great host and we had everything we needed. Melissa and Jason South Carolina"
The price is CA $177
CA $230 total
includes taxes & fees
Feb 24 - Feb 25
Guest House with acreage to explore.

Mary - C · Central, Floor Level 2bd/2ba Apt w/Pool & WiFi

9.8 out of 10, Exceptional, (8)
"The apartment is conveniently located near many businesses. The rental was clean, and all directions provided were clear and concise and easy to follow. Jada was easy to work with and communicate with and resolved any questions/concerns I had. Great property! "
The price is CA $154
CA $351 total
includes taxes & fees
Mar 9 - Mar 10
Mary - C · Central, Floor Level 2bd/2ba Apt w/Pool & WiFi

Comfortable house where guests feel welcome. 10 minutes from Evansville Airport

6.0 out of 10, (2)
"Our stay at the house was absolutely incredible. The location, amenities, and hospitality were top-notch. The place was spotless and beautifully decorated, with every detail carefully thought out. The kitchen was fully equipped, and the house is located in a safe area. The host was incredibly welcoming and provided us with all the information we needed for a smooth check-in. They even left a welcome basket for us, which was a lovely touch."
Comfortable house where guests feel welcome. 10 minutes from Evansville Airport

Cozy Cottage, 3 mins from EVV, fenced yard

10.0 out of 10, Exceptional, (9)
"We were just in for a quick weekend stay. The house was perfect for us and very clean. Host is very punctual for communication and was very accommodating for us! The yard was wonderful for our pups. Clean up bags were also provided which was perfect since we forgot ours. The pups enjoyed running all over the yard tiring themselves out for the evening! There is a fire pit that we definitely would have used had we stayed longer. A place we would highly recommend if headed to the Evansville area! "
Cozy Cottage, 3 mins from EVV, fenced yard

Fenced-In Yard on the East Side

10.0 out of 10, Exceptional, (8)
"Overall the house was very nice and in a great spot for the concert we attended."
The price is CA $213
CA $403 total
includes taxes & fees
Mar 23 - Mar 24
Fenced-In Yard on the East Side

Vibrant and art-filled retreat, perfect for families and small groups.

2.0 star property
9.2 out of 10, Wonderful, (5)
"Enjoyed the house. Had friends for dinner one night and family the next fay for our hilday get together. The house is cute, clean and had everything we needed. Tge host was readily available when we had questions. I would definitely stay again!"
Vibrant and art-filled retreat, perfect for families and small groups.

BRAND NEW: Oakside Retreat with MASSIVE Yard & High End Amenities

10.0 out of 10, Exceptional, (4)
"Bobby’s place was perfect for our family stay in Evansville. The location was convenient and the house was exactly as described - clean and comfortable. Would def stay here again!"
BRAND NEW: Oakside Retreat with MASSIVE Yard & High End Amenities
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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Other types of properties in Oakland City you may be interested in

< 1 Mi to Oakland City University: Quiet Studio

< 1 Mi to Oakland City University: Quiet Studio

Spark by Hilton Evansville East, IN

2.5 star property
9.0 out of 10, Wonderful, (54)
"It was a very nice stay and served its purpose for an overnight stay. Our refrigerator made a weird noise and we reported it when we checked out so they could look into it. The room was extremely spacious and had room for extra furniture. It had several open spaces for storage. The only two things we didn’t really like was that our room did not have an outlet by the sink for the hair dryer and you had to unplug the tv in the main room to plug in the hair dryer. There was a full length...
The price is CA $108
CA $125 total
includes taxes & fees
Mar 2 - Mar 3
Spark by Hilton Evansville East, IN

Country Inn & Suites by Radisson, Evansville, IN

3.0 star property
8.6 out of 10, Excellent, (1005)
"Good"
The price is CA $118
CA $136 total
includes taxes & fees
Mar 16 - Mar 17
Country Inn & Suites by Radisson, Evansville, IN
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.

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?

The Potter Cottage -A great family getaway 3 miles from Holiday World: This vacation home rental near Oakland City is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease 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. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Oakland City?

While you're exploring the area, Bridlewood Park and Wabash Erie Canal Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll also find Oakland City University.

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.