Oakland City Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Oakland City vacation rentals

Interior

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, (22 reviews)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
$174 nightly
The price is $195
Jan 31 - Feb 1
Total with taxes and fees
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Smart TV, books

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.8 out of 10, Exceptional, (34 reviews)
"Great stay!"
United States
Kristi M.
$248 nightly
The price is $271
Feb 2 - Feb 3
Total with taxes and fees
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Fridge, microwave, oven, stovetop

Barn in the Burgh

Barn in the Burgh
Newburgh
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful warm cozy place. We stayed due to a funeral and it is the perfect place wind down and relax. Planning to come back again! "
United States
Rebecca P.
$345 nightly
The price is $378
Feb 2 - Feb 3
Total with taxes and fees
Barn in the Burgh
Outdoor dining

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (13 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
$217 nightly
The price is $238
Feb 1 - Feb 2
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Smart TV

Trendy Two bedroom home centrally located near UE

Trendy Two bedroom home centrally located near UE
Evansville
9.2 out of 10, Wonderful, (5 reviews)
"Place was very clean. Provisions were great! We were glad to be able to do laundry. We suggest having a laundry basket and a small folding table."
United States
Carol B.
$146 nightly
The price is $168
Feb 5 - Feb 6
Total with taxes and fees
Trendy Two bedroom home centrally located near UE
Interior

Tranquil Hideaway: Your Private Lakefront Retreat

Tranquil Hideaway: Your Private Lakefront Retreat
Dale
9.4 out of 10, Exceptional, (14 reviews)
"This property is amazing! We loved the privacy and peacefulness. The house is great and we will definitely be coming back!"
United States
Natalie S.
$243 nightly
The price is $266
Jan 31 - Feb 1
Total with taxes and fees
Tranquil Hideaway: Your Private Lakefront Retreat
Property grounds

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.6 out of 10, Exceptional, (18 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
$217 nightly
The price is $238
Feb 1 - Feb 2
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Smart TV

Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (61 reviews)
"The cabin was super cozy and comfortable! "
United States
Kellie J.
$145 nightly
The price is $159
Jan 31 - Feb 1
Total with taxes and fees
Guest House with acreage to explore.
TV

Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (19 reviews)
"The cabin was a cozy place to stay and close enough to holiday world without the headache of keeping my younger kids silent like I would have if we stayed in a hotel! Very clean and organized! "
United States
Ashley J.
$246 nightly
The price is $269
Feb 1 - Feb 2
Total with taxes and fees
Yellow Banks Log Cabin with Lake Views
2 bedrooms, desk, WiFi

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.
$189 nightly
The price is $218
Feb 1 - Feb 2
Total with taxes and fees
The Chic Shack | Centrally Located 2BR/1BA Home
Smart TV

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.
$187 nightly
The price is $215
Feb 1 - Feb 2
Total with taxes and fees
Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything
2 bedrooms, iron/ironing board, WiFi, bed sheets

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
$164 nightly
The price is $189
Feb 1 - Feb 2
Total with taxes and fees
2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer
Smart TV, fireplace

Perfect industrial studio in charming downtown Boonville

Perfect industrial studio in charming downtown Boonville
Boonville
$115 nightly
The price is $128
Jan 31 - Feb 1
Total with taxes and fees
Perfect industrial studio in charming downtown Boonville
Fridge, microwave, oven, stovetop

5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.6 out of 10, Exceptional, (15 reviews)
"Perfect place to stay when a big space is needed"
United States
Joel Z.
$343 nightly
The price is $384
Feb 1 - Feb 2
Total with taxes and fees
5 Miles from Holiday World sleeps 11+ —Family Escape
Smart TV

Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (1 review)
$280 nightly
The price is $313
Jan 31 - Feb 1
Total with taxes and fees
Family Friendly Lakehouse with great views!
Outdoor dining

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.4 out of 10, Exceptional, (21 reviews)
"Very nice cabin very clean overall really enjoyed"
United States
Addy D.
$217 nightly
The price is $238
Feb 1 - Feb 2
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
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

Oakland Courtyard

Oakland Courtyard

10/10 Excellent
"Lady at front desk was very nice"
Christopher 1-night trip
Posted 5 days ago
Oakland Courtyard

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 $159 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.

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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?

Tranquil Hideaway: Your Private Lakefront Retreat: This vacation home near Oakland City is located on the waterfront and has a fireplace, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Oakland City?

Visit the sights while you're exploring the area such as Oakland City University and Wabash Erie Canal Park.

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.