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Oakland City Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Oakland City vacation rentals

A bedroom with a wooden wall panel, a bed with white bedding, and a small shelf with decorative items.

1. Princeton Suite 7 - QUEEN 1BD/1BA Apt

Princeton Suite 7 - QUEEN 1BD/1BA Apt
Princeton
The price is AED 304
AED 616 total
includes taxes & fees
10 Nov - 11 Nov
Princeton Suite 7 - QUEEN 1BD/1BA Apt
A cozy cabin interior with a sofa, dining table, and chairs.

2. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (29 reviews)
"A nice little cabin for our trip to holiday world."
United States
Brandon R.
The price is AED 643
AED 1,074 total
includes taxes & fees
5 Nov - 6 Nov
Yellow Banks Log Cabin with Lake Views
A rustic wooden building with a covered porch and a picnic table.

3. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.8 out of 10, Exceptional, (8 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 AED 569
AED 938 total
includes taxes & fees
11 Nov - 12 Nov
Yellow Banks Log Cabin With Waterfront Views
A door with two windows, each with horizontal blinds, leading to a view of a grassy area and a body of water.

4. Tranquil Hideaway: Your Private Lakefront Retreat

Tranquil Hideaway: Your Private Lakefront Retreat
Dale
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.
The price is AED 463
AED 1,115 total
includes taxes & fees
17 Nov - 18 Nov
Tranquil Hideaway: Your Private Lakefront Retreat
A wooden interior with a television, wooden cabinets, and a plant.

5. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (74 reviews)
"Nice quaint place to stay. 10/10 would recommend and stay if in the area again"
United States
Chasity D.
The price is AED 525
AED 642 total
includes taxes & fees
5 Nov - 6 Nov
Guest House with acreage to explore.
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

6. 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, (30 reviews)
"Me and my family stayed while visiting holiday world and we highly recommend. Prices was affordable and the host was great."
United States
James B.
The price is AED 364
AED 683 total
includes taxes & fees
6 Nov - 7 Nov
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A compact kitchen with wooden cabinets, a stainless steel refrigerator, an oven, a microwave, a sink, and a kettle. There is a dining table with chairs.

7. 5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.8 out of 10, Exceptional, (35 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is AED 909
AED 1,442 total
includes taxes & fees
8 Nov - 9 Nov
5 Miles from Holiday World sleeps 11+ —Family Escape
A spacious living room with a wooden coffee table, a TV mounted on the wall, and a ceiling fan.

8. Barn in the Burgh — Barndominium Sleeps 12 · Game Room

Barn in the Burgh — Barndominium Sleeps 12 · Game Room
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is AED 647
AED 1,824 total
includes taxes & fees
30 Nov - 1 Dec
Barn in the Burgh — Barndominium Sleeps 12 · Game Room
A dining area with a stone fireplace, a table with chairs, and a kitchen in the background.

9. Cozy Cottage, 3 mins from EVV, fenced yard

Cozy Cottage, 3 mins from EVV, fenced yard
Evansville
9.8 out of 10, Exceptional, (29 reviews)
"It was a nice place for a multigenerational family to stay for a university graduation."
United States
Jennifer R.
The price is AED 1,194
AED 2,636 total
includes taxes & fees
28 Nov - 29 Nov
Cozy Cottage, 3 mins from EVV, fenced yard
A neatly made bed with rolled towels, a patterned throw, and a yellow pillow.

10. RiverStone Retreat A

RiverStone Retreat A
Newburgh
8.8 out of 10, Excellent, (3 reviews)
"The host was very prompt on his responses. The apartment was very well maintained and clean. There are only a couple of glasses so that would be the only thing I'd change. Overall great experience. Me and my partner want to stay next time we get a VRBO 10/10"
United States
Unspecified U.
RiverStone Retreat A
A modern living room with a sofa, ottoman, and a coffee table.

11. Near Deaconess & Ford Center, pet friendly, wifi

Near Deaconess & Ford Center, pet friendly, wifi
Evansville
Near Deaconess & Ford Center, pet friendly, wifi
A neatly made bed with a white duvet and a yellow throw, a bedside table with a lamp, and decorative wall art.

12. 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.
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
A spacious living room with a fireplace, a dining area with wooden furniture, and a kitchen with wooden cabinets.

13. Retro '90s 2BR/2BA • Private Entrance • Pet-Friendly • King Bed • 5 M...

Retro '90s 2BR/2BA • Private Entrance • Pet-Friendly • King Bed • 5 M...
Newburgh
10.0 out of 10, Exceptional, (2 reviews)
"Nathan was very responsive to our changing plans and understanding. Will definitely stay here on future visits to Southern Indiana."
United States
Chad K.
Retro '90s 2BR/2BA • Private Entrance • Pet-Friendly • King Bed • 5 M...
A single-story house with a gabled roof, white shutters, and a front porch.

14. 3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World

3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Ferdinand
10.0 out of 10, Exceptional, (4 reviews)
"The property was conveniently located within all of our planned attractions."
United States
Lavar B.
The price is AED 576
AED 921 total
includes taxes & fees
9 Nov - 10 Nov
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

15. 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, (15 reviews)
"Nicely decorated with top amenities. Lovely beds and linens. Worked out perfect for our family"
United States
Lori M.
The price is AED 951
AED 2,336 total
includes taxes & fees
11 Nov - 12 Nov
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

16. Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.6 out of 10, Exceptional, (45 reviews)
"Great location, quiet but still close to shopping and restaurants. Use of the garage was a plus as it was raining the day we were packing up to leave."
United States
chris g.
The price is AED 370
AED 1,032 total
includes taxes & fees
8 Nov - 9 Nov
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
A modern living room with a white sofa, a black leather chair, a wooden coffee table, and a dining area in the background.

17. Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything

Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything
Evansville
7.8 out of 10, Good, (7 reviews)
"We arrived around 8:30pm to find sleeping arrangements for 4 adults. The couch is about 4' long. We chose this place because it is listed as sleeping 5, but it's not. We woke up in the morning to shower and found a pitiful excuse of a shower. It dripped water. I took a video but unfortunately there is nowhere to upload it. It was sad. As if this wasn't enough, the kitchen utensils on the stove were covered in dried food and the vanity in the shower was not secure and fell off and landed on my...
United States
Sam S.
Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything
A living room with a TV, sofa, coffee table, and a dining area with a chair and table.

18. Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!

Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
Evansville
The price is AED 272
AED 748 total
includes taxes & fees
9 Nov - 10 Nov
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
A spacious living room with a fireplace, a large window, and a high ceiling with exposed beams.

19. Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (15 reviews)
"Very beautiful and comfortable house for our stay"
United States
James S.
The price is AED 1,230
AED 1,485 total
includes taxes & fees
9 Nov - 10 Nov
Family Friendly Lakehouse with great views!
A modern kitchen with wooden flooring, stainless steel appliances, a dining area with a view, and a 'GROCERY' sign.

20. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (13 reviews)
"Family friendly, close to holiday world!"
United States
Amy M.
The price is AED 1,309
AED 1,935 total
includes taxes & fees
17 Nov - 18 Nov
Run Away Reindeer Retreat
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

Comfort Inn Evansville East

Comfort Inn Evansville East

10/10 Excellent
"Friendly staff"
Robert 3-night trip
Posted 7 hours ago
Comfort Inn Evansville East

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?

Oakside Retreat – Private Getaway with Huge Yard, Firepit and Game Room: This vacation home rental near Oakland City offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable 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.

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.