Oakland City Vacation Rentals

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Vacation Rentals in Oakland City

Guest House with acreage to explore.
Property grounds
Guest House with acreage to explore.
9.6 out of 10, Exceptional, (46)
"Place was as described and perfect for us. Clean, comfortable and host was great with communication. Between the two of us we caught over 30 fish in the pond. Very fun. Thank you for a great stay "
The price is CA $175
CA $227 total
includes taxes & fees
Nov 25 - Nov 26
Guest House with acreage to explore.
Vibrant and art-filled retreat, perfect for families and small groups.
Property grounds
Vibrant and art-filled retreat, perfect for families and small groups.
2.0 star property
8.0 out of 10, Very good, (1)
"Nice clean stay for a quick weekend and close to downtown. "
Vibrant and art-filled retreat, perfect for families and small groups.
Yellow Banks Log Cabin with Lake Views
Dining
Yellow Banks Log Cabin with Lake Views
9.2 out of 10, Wonderful, (11)
"Nice secluded area, very tranquil setting "
The price is CA $210
CA $383 total
includes taxes & fees
Nov 24 - Nov 25
Yellow Banks Log Cabin with Lake Views
Yellow Banks Log Cabin With Waterfront Views
Smart TV
Yellow Banks Log Cabin With Waterfront Views
9.6 out of 10, Exceptional, (11)
"The cabin was a nice visit and housed our family. There is a fire pit and a little pond that has some bluegill fish in it. The upstairs can get warm but had to set the living room fan to push the cold air up."
The price is CA $175
CA $338 total
includes taxes & fees
Nov 24 - Nov 25
Yellow Banks Log Cabin With Waterfront Views
Cozy Bungalow in a nice friendly neighborhood
Fridge, microwave, oven, stovetop
Cozy Bungalow in a nice friendly neighborhood
9.8 out of 10, Exceptional, (57)
"I rented this great bungalow for my son and Grandson, who had a hockey weekend. They loved the house, and it was very convenient to get to the ice rinks, and other attractions in Evansville. My son said the beds were really comfy! "
Cozy Bungalow in a nice friendly neighborhood
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Fridge, microwave, oven, stovetop
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
10.0 out of 10, Exceptional, (8)
"We stayed overnight after going to Holiday World. The listing was accurate and the accommodations were clean and ready. Very enjoyable stay!"
The price is CA $186
CA $294 total
includes taxes & fees
Nov 27 - Nov 28
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Yellow Banks Log Cabin With Waterfront Views
Interior
Yellow Banks Log Cabin With Waterfront Views
10.0 out of 10, Exceptional, (6)
"This place was great, and peaceful. I'll definitely be staying here anytime my family visits holiday world. Almost spent our second day just at the cabin. So relaxing."
The price is CA $175
CA $334 total
includes taxes & fees
Nov 25 - Nov 26
Yellow Banks Log Cabin With Waterfront Views
Comfort and Charm Highly Recommended
Fridge, microwave, oven, stovetop
Comfort and Charm Highly Recommended
9.6 out of 10, Exceptional, (12)
"We stayed here for a weekend and it was a pleasant stay. It was cute, charming, and a good size. The host was very communicative and left plenty of snacks for us, which was great! The house is in a great location and was presented to us in superb condition. Would highly recommend this place!"
Comfort and Charm Highly Recommended
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
Aerial view
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
10.0 out of 10, Exceptional, (14)
"House was clean had everything we needed. Neighborhood was quiet and relaxing. Perfect weekend getaway "
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Interior
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
9.8 out of 10, Exceptional, (24)
"Great house. Everything you will need for your stay. Owners are super nice. Turkeys and deer in the yard in the evening. I will try to stay here anytime i'm in that area."
The price is CA $142
CA $407 total
includes taxes & fees
Dec 23 - Dec 24
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
The Family Oasis just 6 miles from Holiday World
Property grounds
The Family Oasis just 6 miles from Holiday World
9.2 out of 10, Wonderful, (33)
"The place was amazing. Very nice place to stay for the weekend "
The Family Oasis just 6 miles from Holiday World
Charming 2-bedroom lake house in Dale
TV, fireplace
Charming 2-bedroom lake house in Dale
The price is CA $113
CA $285 total
includes taxes & fees
Nov 27 - Nov 28
Charming 2-bedroom lake house in Dale
Cozy Cottage, 3 mins from EVV, fenced yard
Interior
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
BRAND NEW: Oakside Retreat with MASSIVE Yard & High End Amenities
Interior
BRAND NEW: Oakside Retreat with MASSIVE Yard & High End Amenities
10.0 out of 10, Exceptional, (1)
"Our group of 6 enjoyed our overnight stay. It was a quick drive to the Ford Center for a concert. There was a little hiccup with the key code, but the owner was quick to respond and fix the problem."
The price is CA $175
CA $495 total
includes taxes & fees
Dec 10 - Dec 11
BRAND NEW: Oakside Retreat with MASSIVE Yard & High End Amenities
River View in Downtown Newburgh
Exterior
River View in Downtown Newburgh
9.0 out of 10, Wonderful, (2)
"The views of the Ohio River were beautiful. Lots of steps up to house but the views were worth it! House was clean and neat…gorgeous furniture. Our grandchildren especially loved the games in the library room. We also loved being able to seat the whole family at dining table for meals. Lovely home. "
River View in Downtown Newburgh
Mary - C · Central 2bd/2ba Apt w/Pool &WiFi
Fridge, microwave, oven, stovetop
Mary - C · Central 2bd/2ba Apt w/Pool &WiFi
10.0 out of 10, Exceptional, (3)
"The property manager was very sweet and made sure we were comfortable/had the things we needed throughout our stay. "
The price is CA $126
CA $335 total
includes taxes & fees
Nov 23 - Nov 24
Mary - C · Central 2bd/2ba Apt w/Pool &WiFi
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
Fridge, microwave, oven, stovetop
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
10.0 out of 10, Exceptional, (6)
"Was much better than staying in a hotel"
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
Enchanting historical home with River View
Fridge, microwave, oven, stovetop
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 $196
CA $472 total
includes taxes & fees
Nov 26 - Nov 27
Enchanting historical home with River View
Yellow Banks Log Cabin With Waterfront Views
Property grounds
Yellow Banks Log Cabin With Waterfront Views
9.8 out of 10, Exceptional, (8)
"The location was perfect for our trip to Holiday World. The surrounding property is beautiful and and was perfect for a bonfire. We had lots of fun embracing the aspects of cabin living. Enough space for 5 college friends :)"
The price is CA $175
CA $338 total
includes taxes & fees
Nov 24 - Nov 25
Yellow Banks Log Cabin With Waterfront Views
Another Oasis just 6 miles from Holiday World
Exterior
Another Oasis just 6 miles from Holiday World
8.8 out of 10, Excellent, (10)
"This house was amazing! The house was way bigger then we could of imagined. My whole family came and everyone had their own space. The bedrooms and closets are huge. The best part was the outside area. The host was gracious and quick to help with any issue. We will definitely be back. "
Another Oasis just 6 miles from Holiday World
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

Country Inn & Suites by Radisson, Evansville, IN
Lobby
Country Inn & Suites by Radisson, Evansville, IN
3.0 star property
8.6 out of 10, Excellent, (1001)
"Convenient and close"
The price is CA $105
CA $121 total
includes taxes & fees
Dec 8 - Dec 9
Country Inn & Suites by Radisson, Evansville, IN
La Quinta Inn & Suites by Wyndham Evansville
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, (1002)
"I am here for work a second time. As always I stay at the LaQuinta for months until my contract ends when I’m in the area. The place is NICE, affordable & the staff is AMAZING. Great breakfast and pet friendly so I don’t have to leave my baby home when I travel! Highly recommended ❤️"
The price is CA $106
CA $122 total
includes taxes & fees
Nov 25 - Nov 26
La Quinta Inn & Suites by Wyndham Evansville
Drury Inn & Suites Evansville East
Lobby
Drury Inn & Suites Evansville East
3.0 star property
9.2 out of 10, Wonderful, (1003)
"All fine , no issues, would recommend "
The price is CA $140
CA $161 total
includes taxes & fees
Nov 26 - Nov 27
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.
Beautiful view of the beach with palm trees

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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?

2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!! : Located near Oakland City, this vacation home rental is located next to a golf course and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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?

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.