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Oakland City Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oakland City holiday rentals

A two-story house with a front porch, two chairs, and a stone pillar.

1. THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Lynnville
9.8 out of 10, Exceptional, (16 reviews)
"Very attentive host. Good value. This house was perfect for our group's trip to Holiday World. We're looking at staying again in the future."
United States
Patricia G.
The price is NZ$505
includes taxes & fees
28 Sept - 29 Sept
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A wooden cabin with a porch, a picnic table, and a fire pit.

2. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (35 reviews)
"We had a great time and enjoyed our stay!"
United States
Anonymous traveller
The price is NZ$416
includes taxes & fees
27 Sept - 28 Sept
Yellow Banks Log Cabin With Waterfront Views
A wooden gazebo with a gravel path leading to a pond, surrounded by trees and a grassy area.

3. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (24 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
The price is NZ$471
includes taxes & fees
27 Sept - 28 Sept
Yellow Banks Log Cabin With Waterfront Views
A rustic wooden building with a covered porch and a picnic table.

4. 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 NZ$481
includes taxes & fees
27 Sept - 28 Sept
Yellow Banks Log Cabin With Waterfront Views
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, (73 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
The price is NZ$319
includes taxes & fees
26 Sept - 27 Sept
Guest House with acreage to explore.
A cozy cabin interior with a sofa, dining table, and chairs.

6. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (29 reviews)
"Great cabin! Comfy beds."
United States
Kelly G.
The price is NZ$526
includes taxes & fees
27 Sept - 28 Sept
Yellow Banks Log Cabin with Lake Views
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

7. 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, (29 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 NZ$340
includes taxes & fees
27 Sept - 28 Sept
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

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

Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is NZ$685
includes taxes & fees
30 Sept - 1 Oct
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

9. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
10.0 out of 10, Exceptional, (1 review)
"We had an excellent stay! Place was nice and homey, well decorated and perfectly clean! Host was on top of making sure we had everything we needed. Would definitely recommend for anyone wanting to stay close to Holiday World or Lincoln State Park!"
United States
Jennifer C.
The price is NZ$698
includes taxes & fees
29 Sept - 30 Sept
The Cowboys Slumber' 2 Mi to Lincoln State Park
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

10. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
3.0 star property
Gentryville
The price is NZ$688
includes taxes & fees
28 Sept - 29 Sept
The Cowboys Slumber' 2 Mi to Lincoln State Park
A wooden cabin with a covered porch, a picnic table, and a view of a lake.

11. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.0 out of 10, Wonderful, (17 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is NZ$471
includes taxes & fees
27 Sept - 28 Sept
Yellow Banks Log Cabin With Waterfront Views
A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

12. 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, (44 reviews)
"We have absolutely loved it here the wildlife the owners are amazing. I hope that next time we’re in town will be able to stay here again."
United States
Kristen J.
The price is NZ$497
includes taxes & fees
8 Oct - 9 Oct
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
A neatly made bed with rolled towels, a patterned throw, and a yellow pillow.

13. RiverStone Retreat A

RiverStone Retreat A
Newburgh
8.8 out of 10, Excellent, (3 reviews)
The price is NZ$291
includes taxes & fees
27 Sept - 28 Sept
RiverStone Retreat A
A modern living room with a sectional sofa, a coffee table, and decorative plants.

14. Trendy Two bedroom home centrally located near UE

Trendy Two bedroom home centrally located near UE
Evansville
9.0 out of 10, Wonderful, (11 reviews)
"Would stay again"
United States
Scott D.
The price is NZ$340
includes taxes & fees
30 Sept - 1 Oct
Trendy Two bedroom home centrally located near UE
A neatly made bed with a yellow throw blanket, white bedding, and decorative pillows. There are two bedside tables with lamps, a wall-mounted light, and two abstract paintings above the bed.

15. Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh

Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
Newburgh
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Adam B.
The price is NZ$355
includes taxes & fees
27 Sept - 28 Sept
Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
A living room with a TV, sofa, coffee table, and a dining area with a chair and table.

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

Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
Evansville
The price is NZ$387
includes taxes & fees
5 Oct - 6 Oct
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
A modern hotel room with a large flat-screen TV, a dining area with a chandelier, and a cozy seating arrangement.

17. The Chic Shack | Centrally Located 2BR/1BA Home

The Chic Shack | Centrally Located 2BR/1BA Home
Evansville
10.0 out of 10, Exceptional, (2 reviews)
"It felt like home in this space. All the extra throw blankets to be warm and cozy. The host is very easy to work with."
United States
Meisha W.
The price is NZ$376
includes taxes & fees
27 Sept - 28 Sept
The Chic Shack | Centrally Located 2BR/1BA Home
A modern bedroom with a large bed, a bedside table with a lamp, and a window with curtains.

18. 2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer

2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer
Evansville
2.0 out of 10, (1 review)
"This property is not what you see in the pictures. It's shabby and rough inside, including missing molding, patched walls and scuffed up furniture. We walked in and there were flies all over the kitchen and dead on the counter. It probably was a temporary problem, but not something you want to walk in on when you're paying for the space. The beds were made, but not sure that the house had been cleaned recently based on the kitchen. The outside of the house is also rough. Parking on the...
United States
Heather M.
The price is NZ$338
includes taxes & fees
28 Sept - 29 Sept
2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer
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.

19. 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, (33 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is NZ$755
includes taxes & fees
1 Oct - 2 Oct
5 Miles from Holiday World sleeps 11+ —Family Escape
A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

20. 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, (13 reviews)
"Property was as advertised - Ryan was excellent to work with. I wouldn’t hesitate to stay at this property again!"
United States
Jacob O.
The price is NZ$942
includes taxes & fees
4 Oct - 5 Oct
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
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 Jasper South

Comfort Inn Jasper South

10/10 Excellent
"Everything was good! Staff was very helpful! Room was clean,"
Adrienne 1-night trip
Posted 1 hour ago
Comfort Inn Jasper South

Find out more about Oakland City

Everything you need to know about Oakland City holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland City holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland City holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland City holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland City. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland City holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland City holiday rentals we have selected for you start as low as NZ$319 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland City rentals

At Expedia, we put the best Oakland City holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland City holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Oakland City?

Yes, there are holiday rentals close to the most popular sights in Oakland City, or you can select a more secluded option if you're looking for a relaxing stay. Oakland City is known for its restaurants and university setting.

What are some of the best holiday rentals that Oakland City has to offer?

Oakside Retreat – Private Getaway with Huge Yard, Firepit and Game Room: This holiday home rental outside of Oakland City offers a selection of games, a BBQ 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 that 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 holiday rentals like in Oakland City?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland City. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.