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Oakland City Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Oakland City vacation 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 CA $203
CA $411 total
includes taxes & fees
Oct 6 - Oct 7
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A rustic wooden building with a covered porch and a picnic table.

2. 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 CA $220
CA $397 total
includes taxes & fees
Oct 4 - Oct 5
Yellow Banks Log Cabin With Waterfront Views
A wooden cabin with a covered porch, a picnic table, and a view of a lake.

3. 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 CA $213
CA $387 total
includes taxes & fees
Oct 4 - Oct 5
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.

4. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (24 reviews)
"Great location,very clean and cozy!"
United States
Briley E.
The price is CA $213
CA $387 total
includes taxes & fees
Oct 4 - Oct 5
Yellow Banks Log Cabin With Waterfront Views
A cozy cabin interior with a sofa, dining table, and chairs.

5. 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 CA $248
CA $432 total
includes taxes & fees
Oct 4 - Oct 5
Yellow Banks Log Cabin with Lake Views
A wooden interior with a television, wooden cabinets, and a plant.

6. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (74 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
The price is CA $203
CA $259 total
includes taxes & fees
Oct 1 - Oct 2
Guest House with acreage to explore.
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

7. 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 CA $213
CA $559 total
includes taxes & fees
Oct 1 - Oct 2
The Cowboys Slumber' 2 Mi to Lincoln State Park
A room with a blue sofa, wooden tables, and chairs, a round wall clock, and a white ceiling.

8. Princeton Suite 6 - KING 2BR/2BA

Princeton Suite 6 - KING 2BR/2BA
Princeton
2.0 out of 10, (1 review)
The price is CA $128
CA $277 total
includes taxes & fees
Oct 4 - Oct 5
Princeton Suite 6 - KING 2BR/2BA
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

9. 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 CA $140
CA $276 total
includes taxes & fees
Oct 12 - Oct 13
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A wooden cabin with a porch, a picnic table, and a fire pit.

10. 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 CA $177
CA $340 total
includes taxes & fees
Oct 1 - Oct 2
Yellow Banks Log Cabin With Waterfront Views
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

11. 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 CA $156
CA $572 total
includes taxes & fees
Oct 1 - Oct 2
The Cowboys Slumber' 2 Mi to Lincoln State Park
A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

12. 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 CA $192
CA $617 total
includes taxes & fees
Oct 4 - Oct 5
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A modern living room with a sectional sofa, a coffee table, and decorative plants.

13. 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 CA $119
CA $274 total
includes taxes & fees
Oct 5 - Oct 6
Trendy Two bedroom home centrally located near UE
A modern hotel room with a large flat-screen TV, a dining area with a chandelier, and a cozy seating arrangement.

14. 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 CA $145
CA $307 total
includes taxes & fees
Oct 4 - Oct 5
The Chic Shack | Centrally Located 2BR/1BA Home
A neatly made bed with rolled towels, a patterned throw, and a yellow pillow.

15. 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 CA $121
CA $249 total
includes taxes & fees
Oct 6 - Oct 7
RiverStone Retreat A
A neatly made bed with a white duvet and a yellow throw, a bedside table with a lamp, and decorative wall art.

16. 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 CA $139
CA $289 total
includes taxes & fees
Oct 4 - Oct 5
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
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.
The price is CA $133
CA $290 total
includes taxes & fees
Oct 1 - Oct 2
Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything
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.

18. 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, (34 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is CA $383
CA $624 total
includes taxes & fees
Oct 4 - Oct 5
5 Miles from Holiday World sleeps 11+ —Family Escape
A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

19. 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 CA $130
CA $393 total
includes taxes & fees
Oct 8 - Oct 9
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
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 CA $240
CA $781 total
includes taxes & fees
Oct 8 - Oct 9
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

Baymont by Wyndham Washington

Baymont by Wyndham Washington

10/10 Excellent
"Extremely friendly and helpful staff."
Melissa 1-night trip
Posted 9 hours ago
Baymont by Wyndham Washington

Find out more about Oakland City

Everything you need to know about Oakland City vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland City vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland City vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland City vacation rentals we have selected for you start as low as CA $259 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 vacation 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 vacation.

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. 

Explore a world of travel with Expedia

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.