Oakland City Vacation Rentals

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Vacation Rentals in Oakland City

Property grounds
Rustic Guest House with acreage to explore.
9.6 out of 10, Exceptional, (33)
"Doug was awesome! The property had probably the best bed we have slept in. He was thoughtful and had some protectors for the couches knowing we had a couple dogs with us. It was nice and quiet out at his place though we didn't get to explore because of family obligations. My car decided to die on us and he was so kind offering help and not mad about the circumstance of essentially checking out a hour late due to having to run into town and back for a new battery. We greatly appreciate his...
The price is CA $171
CA $222 total
includes taxes & fees
May 28 - May 29
Rustic Guest House with acreage to explore.
Property grounds
The Family Oasis just 6 miles from Holiday World
8.8 out of 10, Excellent, (18)
"Excellent location, quiet, clean with nice thoughtful touches to make a welcoming stay. Perfect place to have a weekend getaway."
The price is CA $395
CA $634 total
includes taxes & fees
Jun 8 - Jun 9
The Family Oasis just 6 miles from Holiday World
Aerial view
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
10.0 out of 10, Exceptional, (1)
"My family and I booked at the last minute so we could go view the Solar Eclipse. The process of booking, checking in and checking out was a breeze. Jodey was very responsive and extremely helpful in making our stay very enjoyable. We would highly recommend a stay here, and we hope to return for a Christmas visit to Santa Claus."
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
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Fridge, microwave, oven, stovetop
Cozy Bungalow in a nice friendly neighborhood
9.8 out of 10, Exceptional, (50)
"This was a the perfect fit for a short stay in Evansville. The neighborhood was quiet, and I felt very safe staying there. It is just a short 7-minute drive to downtown. The owners were very responsive and answered all of my questions."
Cozy Bungalow in a nice friendly neighborhood
Exterior
Another Oasis just 6 miles from Holiday World
9.0 out of 10, Wonderful, (4)
"We brought our son and his wife and kids to our holiday world mini vacation. There was plenty of space for all of us and lots of space for the kids to run and play. They even had games for the kids. The place was exactly as described. The host was very easy to communicate with and promp with responses. We will definitely plan to stay there again!"
The price is CA $409
CA $655 total
includes taxes & fees
Jun 14 - Jun 15
Another Oasis just 6 miles from Holiday World
Smart TV
Yellow Banks Log Cabin With Waterfront Views
9.6 out of 10, Exceptional, (5)
"Everything was great"
The price is CA $212
CA $386 total
includes taxes & fees
May 28 - May 29
Yellow Banks Log Cabin With Waterfront Views
Private kitchen
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
10.0 out of 10, Exceptional, (1)
"A great fully finished basement with ample room for a group. Wonderful location to stay to enjoy all that Dubois County has to offer."
The price is CA $182
CA $292 total
includes taxes & fees
May 28 - May 29
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Fridge, microwave, oven, stovetop
X Marks the Spot(Blue)1.5 miles from Holiday World
10.0 out of 10, Exceptional, (1)
"Very nice and clean."
X Marks the Spot(Blue)1.5 miles from Holiday World
Fridge, microwave, oven, stovetop
X Marks the Spot (Purple)
X Marks the Spot (Purple)
Fridge, microwave, oven, stovetop
Comfort and Charm Highly Recommended
9.4 out of 10, Exceptional, (8)
"Great place to host family for graduation celebration."
Comfort and Charm Highly Recommended
View from property
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
9.8 out of 10, Exceptional, (19)
"nice and quiet"
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Fridge, microwave, oven, stovetop
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
10.0 out of 10, Exceptional, (4)
"Easy and quick stay Easy of booking on short notice. Very clean and well maintained property. Comfortable bed. As described Thank goodness!!!"
The price is CA $137
CA $344 total
includes taxes & fees
May 28 - May 29
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
Property grounds
Yellow Banks Log Cabin With Waterfront Views
9.8 out of 10, Exceptional, (6)
"My family loved the cabin my oldest daughter is even thinking of booking it in the near future for a little get away. The owner is amazing as I messed up booking days and they went above and beyond to assure we had a place to stay and remained in communication with us until everything was right. All around a great peaceful place we enjoyed it"
The price is CA $212
CA $386 total
includes taxes & fees
May 28 - May 29
Yellow Banks Log Cabin With Waterfront Views
Private kitchen
Sweet Spot in the City
The price is CA $273
CA $479 total
includes taxes & fees
May 28 - May 29
Sweet Spot in the City
Property grounds
Indiana Studio 6 Miles to Downtown Huntingburg
9.4 out of 10, Exceptional, (3)
"We loved our long weekend vacation. The location was fantastic with easy access to holiday world being a short 20 minute drive. Amenities here were awesome with the hot tub being our favorite. The owner was great to talk with, and had some great recommendations for things to check out in the area. Looking forward to coming back."
Indiana Studio 6 Miles to Downtown Huntingburg
Interior
Yellow Banks Log Cabin With Waterfront Views
10.0 out of 10, Exceptional, (3)
"Contact with property manager was awesome, and super easy. He sent me recommendations for nearby food, and even found somewhere i could but fishbait at. The cabin was perfect for my family(2 adults, 5 year old and a 9 year old). My only suggestion is to add a light in the shower, as it get pretty dark inside there. But wonderful place to stay, and wonderful people for Contact. Will def stay again!"
The price is CA $212
CA $386 total
includes taxes & fees
May 28 - May 29
Yellow Banks Log Cabin With Waterfront Views
3 bedrooms, iron/ironing board, travel crib, free WiFi
Chestnut Street Retreat
10.0 out of 10, Exceptional, (26)
"Property was great. Quiet area, clean and comfortable. Would love to come and do it again. A grill outside would be nice."
Chestnut Street Retreat
Fridge, microwave, oven, stovetop
Fenced-In Yard on the East Side
10.0 out of 10, Exceptional, (2)
"Great place to stay, Very clean and comfortable home, Nice quite neighborhood."
The price is CA $196
CA $394 total
includes taxes & fees
Jun 3 - Jun 4
Fenced-In Yard on the East Side
2 bedrooms, desk, iron/ironing board, travel crib
New Construction | New Furnishings | Luxury Unit
10.0 out of 10, Exceptional, (1)
"This unit is absolutely spotless and comfortable. Keith was an incredibly gracious host, and the whole experience was pleasant and easy. I highly recommend this property and host to anyone looking for a comfortable place to stay in Evansville."
The price is CA $239
CA $541 total
includes taxes & fees
May 28 - May 29
New Construction | New Furnishings | Luxury Unit
Exterior
X Marks the Spot (Green)
X Marks the Spot (Green)
Don't see what you're looking for?
See all available properties in Oakland City
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.

Oakland City Vacation Rental Travel Info

Other types of properties in Oakland City you may be interested in

Lobby
Baymont by Wyndham Evansville East
2.5 star property
8.0 out of 10, Very good, (1009)
"Easy to check in."
The price is CA $100
CA $115 total
includes taxes & fees
Jun 2 - Jun 3
Baymont by Wyndham Evansville East
Premium bedding, desk, iron/ironing board, free cribs/infant beds
La Quinta Inn & Suites by Wyndham Evansville
2.5 star property
8.4 out of 10, Very good, (1009)
"The staff was wonderful. They were efficient and easy to talk with. I was very impressed with the features. Nice variety of breakfast items, very clean room and overall property, great shower pressure, and wonderful bathroom lighting. The bed and pillow were some of the most comfortable I have ever had. Left with very positive feelings and a plan to stay there the next time I am in Evansville."
The price is CA $103
CA $119 total
includes taxes & fees
May 30 - May 31
La Quinta Inn & Suites by Wyndham Evansville
Lobby
Drury Inn & Suites Evansville East
3.0 star property
9.2 out of 10, Wonderful, (1004)
"We always choose Drury Inn clean confortabke hosipitality outstandingly "
The price is CA $141
CA $163 total
includes taxes & fees
Jun 2 - Jun 3
Drury Inn & Suites Evansville East
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.

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?

The Family Oasis just 6 miles from Holiday World: Located near Oakland City, this vacation home rental is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. 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 while you're exploring the area such as Oakland City University and Wabash Erie Canal Park.

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.

Recent reviews of Oakland City properties
Expedia verified reviews