Oakland City Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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
$139 nightly
The price is $156
Nov 10 - Nov 11
Total with taxes and fees
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.
$261 nightly
The price is $292
Nov 8 - Nov 9
Total with taxes and fees
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.
$228 nightly
The price is $255
Nov 11 - Nov 12
Total with taxes and fees
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.
$271 nightly
The price is $304
Nov 17 - Nov 18
Total with taxes and fees
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.
$149 nightly
The price is $167
Nov 7 - Nov 8
Total with taxes and fees
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.
$160 nightly
The price is $179
Nov 7 - Nov 8
Total with taxes and fees
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.
$351 nightly
The price is $393
Nov 8 - Nov 9
Total with taxes and fees
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.
$437 nightly
The price is $490
Nov 30 - Dec 1
Total with taxes and fees
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.
$624 nightly
The price is $718
Nov 28 - Nov 29
Total with taxes and fees
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.
$143 nightly
The price is $160
Nov 11 - Nov 12
Total with taxes and fees
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
$308 nightly
The price is $354
Nov 30 - Dec 1
Total with taxes and fees
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.
$180 nightly
The price is $201
Nov 8 - Nov 9
Total with taxes and fees
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.
$367 nightly
The price is $411
Nov 14 - Nov 15
Total with taxes and fees
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.
$224 nightly
The price is $251
Nov 9 - Nov 10
Total with taxes and fees
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.
$488 nightly
The price is $561
Nov 11 - Nov 12
Total with taxes and fees
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.
$251 nightly
The price is $281
Nov 9 - Nov 10
Total with taxes and fees
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.
$173 nightly
The price is $199
Nov 8 - Nov 9
Total with taxes and fees
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
$176 nightly
The price is $202
Nov 9 - Nov 10
Total with taxes and fees
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.
$355 nightly
The price is $398
Dec 1 - Dec 2
Total with taxes and fees
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.
$403 nightly
The price is $441
Dec 7 - Dec 8
Total with taxes and fees
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Oakland City Hotel Reviews

A Holiday Inn Express & Suites hotel with a covered entrance, parking lot, and a well-lit facade.
Holiday Inn Express & Suites Evansville North by IHG

Holiday Inn Express & Suites Evansville North by IHG

Holiday Inn Express & Suites Evansville North by IHG
Evansville

10/10 Excellent

Recently modernized. Loved the great lighting in the room and new sink/bathroom area and comfortable bed.. Very nice lamps and chair. Breakfast was great with sausage, eggs, cheese omelet,sausage gravy and biscuits plus the usual options.
United States
Jana
Reviewed February 1, 2024
Holiday Inn Express & Suites Evansville North by IHG

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Oakland City in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $69 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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.

Explore a world of travel with Expedia