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Oakland City Vacation Rentals

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Check prices for these dates

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

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 ￥11,864
￥24,638 total
includes taxes & fees
Nov 10 - Nov 11
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 ￥27,561
￥46,038 total
includes taxes & fees
Nov 22 - Nov 23
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 ￥24,411
￥42,157 total
includes taxes & fees
Dec 3 - Dec 4
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 ￥19,952
￥48,062 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥22,521
￥27,517 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥15,592
￥28,223 total
includes taxes & fees
Nov 7 - Nov 8
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 ￥38,979
￥61,826 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥27,570
￥77,973 total
includes taxes & fees
Nov 30 - Dec 1
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.
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.
The price is ￥13,121
￥26,046 total
includes taxes & fees
Nov 11 - Nov 12
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
The price is ￥15,245
￥56,471 total
includes taxes & fees
Dec 6 - Dec 7
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.
The price is ￥16,620
￥31,668 total
includes taxes & fees
Nov 9 - Nov 10
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.
The price is ￥18,416
￥67,006 total
includes taxes & fees
Nov 14 - Nov 15
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 ￥24,699
￥39,305 total
includes taxes & fees
Dec 7 - Dec 8
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 ￥31,341
￥88,384 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥15,875
￥44,239 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥11,497
￥31,876 total
includes taxes & fees
Nov 9 - Nov 10
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
A bathroom with a sink, mirror, toilet, and shower curtain.

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 ￥52,097
￥62,960 total
includes taxes & fees
Dec 1 - Dec 2
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 ￥44,976
￥69,404 total
includes taxes & fees
Dec 7 - Dec 8
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

Santas Lodge and Resort

Santas Lodge and Resort

10/10 Excellent
"Awesome stay"
Jessica 1-night trip
Posted 1 day ago
Santas Lodge and Resort

Find out more about Oakland City

Search for holiday rentals in Oakland City on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland City using one of the methods below:

  • View our selection of featured holiday rentals in Oakland City
  • Use the map to find apartments and other holiday homes in the Oakland City neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland City while they last

Look no further and take a look at our great range of rental properties in Oakland City!

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.