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Oakland City Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Oakland City vacation rentals

Smart TV

Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (69 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
$163 nightly
The price is $183
Jul 19 - Jul 20
Total with taxes and fees
Guest House with acreage to explore.
Outdoor dining

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (26 reviews)
"Very nice cabin very clean overall really enjoyed"
United States
Addy D.
$216 nightly
The price is $242
Jul 22 - Jul 23
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Exterior

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.
$249 nightly
The price is $279
Jul 19 - Jul 20
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Smart TV, books

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, (41 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.
$248 nightly
The price is $278
Jul 20 - Jul 21
Total with taxes and fees
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Property grounds

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.6 out of 10, Exceptional, (19 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
$244 nightly
The price is $273
Jul 20 - Jul 21
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
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, (26 reviews)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
$185 nightly
The price is $207
Aug 18 - Aug 19
Total with taxes and fees
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
2 bedrooms, iron/ironing board, WiFi (surcharge), bed sheets

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.
$184 nightly
The price is $206
Jul 20 - Jul 21
Total with taxes and fees
Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
TV

Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.6 out of 10, Excellent, (25 reviews)
"Cute little cabin, fun for kids. "
United States
Paul S.
$275 nightly
The price is $308
Aug 2 - Aug 3
Total with taxes and fees
Yellow Banks Log Cabin with Lake Views
Smart TV, books

Retro 90s 2BR/2BA • Walk to Riverfront • Mins to Deaconess • Travel Nurses

Retro 90s 2BR/2BA • Walk to Riverfront • Mins to Deaconess • Travel Nurses
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.
$358 nightly
The price is $401
Jul 21 - Jul 22
Total with taxes and fees
Retro 90s 2BR/2BA • Walk to Riverfront • Mins to Deaconess • Travel Nurses
Coffee/tea maker, fridge, microwave, oven

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, (8 reviews)
"What a great place to stay. The house is very nice and the area is great. I would definitely stay again. Ryan is great communicating with during the stay. "
United States
Mark B.
$434 nightly
The price is $499
Jul 28 - Jul 29
Total with taxes and fees
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
Exterior

The LC Retreat

The LC Retreat
Lincoln City
10.0 out of 10, Exceptional, (2 reviews)
"We had a comfortable stay and slept well in the comfortable beds with A/C and fans. Close to amusement park and easy to find for making it stress free, so we could relax after a long day."
United States
Hannah D.
$343 nightly
The price is $384
Jul 20 - Jul 21
Total with taxes and fees
The LC Retreat
Exterior

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
10.0 out of 10, Exceptional, (12 reviews)
"Cute quiet lil house located around attractions for families. Well worth the money and host is always available "
United States
Madison B.
$331 nightly
The price is $371
Jul 20 - Jul 21
Total with taxes and fees
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Exterior

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
$340 nightly
The price is $381
Jul 19 - Jul 20
Total with taxes and fees
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Outdoor dining

Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.0 out of 10, Wonderful, (14 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
$244 nightly
The price is $273
Jul 22 - Jul 23
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Fridge, microwave, oven, stovetop

Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
10.0 out of 10, Exceptional, (4 reviews)
"We loved and enjoyed our stay here! The outdoor space is beautiful and peaceful. The inside was so well planned out with lots of cute tiny touches that made it feel so welcoming! We will definitely be returning!"
United States
Marie C.
$488 nightly
The price is $536
Aug 18 - Aug 19
Total with taxes and fees
Run Away Reindeer Retreat
Smart TV

Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (9 reviews)
"This is a very peaceful quiet location and still close to downtown, shops and restaurants. We were there for a wedding in the area, and this was just perfect for the occasion. The house was clean and very welcoming with the open kitchen and living room floor plan. Three of the bedrooms were down the hall away from the noise and then you had beds in the loft, so there was a place for everyone depending on what you wanted. Shout out to our Host, who was very attentive but not intrusive. They...
United States
Christina R.
$372 nightly
The price is $417
Aug 10 - Aug 11
Total with taxes and fees
Family Friendly Lakehouse with great views!
2 bedrooms, iron/ironing board, WiFi (surcharge), bed sheets

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.
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
Smart TV

Harrison Place - Located on Evansville's Eastside

Harrison Place - Located on Evansville's Eastside
Evansville
$480 nightly
The price is $533
Jul 28 - Jul 29
Total with taxes and fees
Harrison Place - Located on Evansville's Eastside
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

Santas Lodge and Resort

Santas Lodge and Resort

10/10 Excellent
"We liked the swimming pools, the hot tub and the breakfast."
Lori 5-night trip
Posted 7 hours ago
Santas Lodge and Resort

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 $183 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.

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?

Run Away Reindeer Retreat: This vacation home rental near Oakland City offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the arcade game room in this rental home to help you unwind.

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.