Oakland City Holiday Rentals from AU$262: Search Short-Term Rentals

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Our top choices for Oakland City holiday 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

includes taxes & fees

1 Nov - 2 Nov

A door with two windows, each with horizontal blinds, leading to a view of a grassy area and a body of water.

2. Tranquil Hideaway: Your Private Lakefront Retreat

Dale

Jim E.

includes taxes & fees

12 Nov - 13 Nov

A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

3. Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Huntingburg

James B.

includes taxes & fees

2 Nov - 3 Nov

A rustic wooden building with a covered porch and a picnic table.

4. Yellow Banks Log Cabin With Waterfront Views

Dale

Ashley J.

includes taxes & fees

1 Nov - 2 Nov

A cozy cabin interior with a sofa, dining table, and chairs.

5. Yellow Banks Log Cabin with Lake Views

Dale

Brandon R.

includes taxes & fees

1 Nov - 2 Nov

A wooden interior with a television, wooden cabinets, and a plant.

6. Guest House with acreage to explore.

Tennyson

Chasity D.

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white cabinetry, stainless steel appliances, and a patterned rug.

7. RiverStone Retreat B

Newburgh

includes taxes & fees

1 Nov - 2 Nov

A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

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

Newburgh

chris g.

includes taxes & fees

31 Oct - 1 Nov

A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

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

Newburgh

Julia F.

includes taxes & fees

2 Nov - 3 Nov

A modern bedroom with a large bed, a bedside table with a lamp, and a window with curtains.

10. 2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer

Evansville

"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...

Heather M.

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a sofa, ottoman, and a coffee table.

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

Evansville

includes taxes & fees

29 Nov - 30 Nov

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.

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

Newburgh

Adam B.

includes taxes & fees

1 Nov - 2 Nov

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.

13. 5 Miles from Holiday World sleeps 11+ —Family Escape

Dale

Darren S.

includes taxes & fees

1 Nov - 2 Nov

A living room with a TV, sofa, coffee table, and a dining area with a chair and table.

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

Evansville

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a fireplace, a large window, and a high ceiling with exposed beams.

15. Family Friendly Lakehouse with great views!

Jasper

James S.

includes taxes & fees

2 Nov - 3 Nov

A single-story house with a gabled roof, white shutters, and a front porch.

16. 3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World

Ferdinand

Lavar B.

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

17. Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy

Evansville

Lori M.

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a dishwasher. There's a small dining area with a table and chairs, and a red sofa in the living room.

18. RiverStone Retreat D

Newburgh

jim a.

A modern kitchen with wooden flooring, stainless steel appliances, a dining area with a view, and a 'GROCERY' sign.

19. Run Away Reindeer Retreat

Clay Township

Amy M.

includes taxes & fees

30 Nov - 1 Dec

A neatly made bed with rolled towels, a patterned throw, and a yellow pillow.

20. RiverStone Retreat A

Newburgh

Unspecified U.

includes taxes & fees

4 Nov - 5 Nov

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Top Oakland City Hotel Reviews

La Quinta Inn & Suites by Wyndham Evansville

8/10 Good

"Check in was a breeze, staff friendly"

Comfort Inn Ferdinand

8/10 Good

"The breakfast was adequate. The room was dusty. The lady said they had been doing construction work in the room and they tried to get all the dust out. The comforter was blood stained. Also there was no shampoo in the dispenser. The lady at the front desk said they were having a hard time finding housekeeping workers. They were down to one that day and the wives of maintenance workers were helping clean the rooms. The people I dealt with at the front desk were very pleasant. The rest of the hotel was clean."

SpringHill Suites by Marriott Newburgh Evansville

8/10 Good

"The room has an odd setup. The bathroom door being straight across from the bed disturbed our sleep. Small counter top didn't work well with hair appliances, makeup and toiletries. And no sink close to the coffee pot was a pain. No side table or coffee table made it hard to sit on the couch with drinks and food. The clothes bar being so low didn't work with our formal clothes. The bed and toilet was too low. Poor room design in my experience from years of traveling. But other than this we had a great experience! Food and coffee was good."

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 favourite 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 depend 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 AU$262 per night. Entering your travel dates in the search wizard might find you 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.

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Check prices for these dates

Our top choices for Oakland City holiday rentals

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

2. Tranquil Hideaway: Your Private Lakefront Retreat

3. Spacious 1450 sf 2 BR Private Suite w/Dog Fe

4. Yellow Banks Log Cabin With Waterfront Views

5. Yellow Banks Log Cabin with Lake Views

6. Guest House with acreage to explore.

7. RiverStone Retreat B

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

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

10. 2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer

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

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

13. 5 Miles from Holiday World sleeps 11+ —Family Escape

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

15. Family Friendly Lakehouse with great views!

16. 3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World

17. Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy

18. RiverStone Retreat D

19. Run Away Reindeer Retreat

20. RiverStone Retreat A

Find holiday rentals that suit your style

Top Oakland City Hotel Reviews

La Quinta Inn & Suites by Wyndham Evansville

Santas Lodge and Resort

Garner Hotel Evansville East by IHG

Comfort Inn Evansville East

Comfort Inn Ferdinand

Drury Inn & Suites Evansville East

SpringHill Suites by Marriott Newburgh Evansville

Hampton Inn Evansville/Airport

Suite Stay Evansville

Find out more about Oakland City

Frequently asked questions

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