Holiday houses in Oakland City

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oakland City

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Top Guest favourite

The single-story home features a charming yellow exterior, complemented by well-maintained grassy areas and large trees providing shade. A spacious driveway leads to a garage, while large windows allow natural light to enter the inviting interior.

Home in Huntingburg

4.99 out of 5 average rating, 171 reviews

Chestnut Street Retreat

A quaint and friendly neighborhood, with large backyard for kids playing, relaxing in the breeze way with morning coffee, or fun by the fire pit. Biking or walking around the neighborhood is safe and fun on a sunny day. Though you may feel in the country you are very close to downtown Huntingburg, 8 miles to Downtown Jasper. House is cozy and relaxing for a weekend away or if you're looking for activities Holiday World (18 Miles), Patoka Lake, French Lick Casino & West Baden Hotel (27 Miles).

FamilyLocationParks

Top Guest favourite

A serene landscape features a lush, green lawn surrounded by trees and two reflective lakes. The tranquil scene invites relaxation under a clear sky, with gentle sunlight filtering through the leaves.

Home in Winslow

5.0 out of 5 average rating, 54 reviews

Twin Lakes

Twin Lakes has a unique location on 60 acres in between 2 wildlife filled lakes stock with fish and wild geese flying in and out. A habitat for deer, squires and rabbits. The house is located down a long drive off the county road in a rural area. Very peaceful to sit on the back deck in the morning and enjoy a cup of coffee and watch the wildlife. Fishermen are invited to enjoy the lake from lakeside or small boat. The home is very comfortable with 2 queen size beds and a futon. Enjoy & relax!

LocationFamilySleep quality

Guest favourite

A cozy master bedroom features warm wooden walls and ceiling, enhancing the natural ambiance. A king-size bed is adorned with a patterned blanket and complemented by wooden furniture. A mirror and map artwork are visible on the walls, with a small window allowing natural light to enter.

Loft in Huntingburg

4.93 out of 5 average rating, 274 reviews

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

ValueLocationKitchen

Top Guest favourite

A view from above captures a six-person hot tub with inviting blue water. Nearby, a circle of Adirondack chairs surrounds a fire pit, all nestled in a wooded area illuminated by warm string lights hanging overhead.

Cabin in Eckerty

4.98 out of 5 average rating, 177 reviews

Whitetail Woods cabin w/ HOT TUB and Patoka pass

Relax with the whole family at this peaceful cabin minutes from Patoka Lake entrance, winery, distillery, brewery, and dining! Perfect for family adventures, romantic getaways, ladies' weekends, and hunting trips. The cabin is located in peaceful Grant Woods surrounded by gorgeous Southern Indiana nature. You'll love relaxing in the 6-person hot tub, rocking on the covered front porch, and roasting marshmallows around the backyard fire pit. Cabin is a short drive to French Lick/West Baden.

LocationFamilyParking

Top Guest favourite

The exterior of a two-story building is showcased, featuring a red metal roof and a balcony with black chairs. A sign hangs above the entrance, while the river and sunset are visible in the background. A pathway runs alongside the building, with parked cars lining the street.

Loft in Newburgh

4.97 out of 5 average rating, 422 reviews

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. Please note that the loft is above a coffee shop that opens at 7am each day and you will hear some noise. 2 complimentary drip coffees are included with your stay!

FamilyValueKitchen

Top Guest favourite

The exterior of a two-story house is shown, featuring a covered porch with two blue chairs. The white siding and gray stone accents create a clean appearance, while well-maintained landscaping complements the inviting entrance. Windows are evenly spaced along the upper and lower levels.

Home in Lynnville

4.98 out of 5 average rating, 52 reviews

The Getaway-3 Bed, 2 Bath, King Bed. Sleeps 6-10

3 Bedroom 2 Bath-Comfortably sleeps 7-10 people. King bed, Queen bed, PackNPlay, Fold Down Couch & Full Air Mattress downstairs. Two Twin XL beds, Daybed, 31x75 Cot & Futon upstairs. Whether you're looking to get away for a wedding weekend, off road riding & hiking at Interlake &/or Sugar Ridge SRA's, or fishing & kayaking at Lynnville Park, this is the perfect location to enjoy all this area of Southern IN has to offer. Easy access to I-64. Large pull through driveway for trailers.

FamilyValueBiking

Guest favourite

A spacious living area features a large sectional sofa in neutral tones, complemented by a cozy accent chair in teal. Two side tables with lamps are positioned beside the sofa. Natural light streams in through two windows, illuminating the soft carpet.

Apartment in Oakland City

5.0 out of 5 average rating, 9 reviews

College Town Comfort

Our 2-bedroom apartment is located in close proximity to Oakland City University. This family friendly retreat offers a cozy and inviting atmosphere for you and your loved ones. With ample space, modern amenities, and a convenient location, it’s the perfect place to relax after a day of exploring the campus and nearby attractions. Whether you’re visiting for a college tour or a business trip, our apartment provides the comfort and convenience you need for an enjoyable getaway.

LocationParkingLong stay

Guest favourite

A cozy living area showcases wooden walls and ceiling, enhancing a rustic feel. The space features a dining table with wooden chairs, a kitchenette with a countertop, and a comfortable seating area with a television. Soft lighting adds warmth to the inviting space.

Guesthouse in Tennyson

4.88 out of 5 average rating, 163 reviews

Guest House with acreage to explore.

Relax with the whole family at this peaceful place to stay. The wooded property provides maintained walking trails for plenty of wildlife viewing pleasure and exercise. The property also features a swimming pond. Location is 8 miles from Lincoln State Park and Lincoln Amphitheater. 10 miles from Interlake State Off Road Recreation Area. 13 miles from Holiday World. 30 miles from Evansville casinos. This is a four season resort/stay, with long summers and mild winters.

ValueFamilyView

Guest favourite

An open living area is highlighted by wooden walls and a loft above. A spacious sofa with a soft throw blanket is present in the foreground, while a dining table and chairs are positioned nearby. Natural light enhances the warm tones of the wood.

Apartment in Fort Branch

4.97 out of 5 average rating, 66 reviews

The Bullpen Suite

Welcome to The Bullpen Suite, a newly remodeled apartment perfect for families and ball players. It features a kid-friendly loft, a cozy bedroom, a full kitchen, bathroom, and a theater-style living room. Enjoy exclusive access to Britton’s Bullpen Fort Branch, just 25 minutes from Deaconess Sports Park. Nearby, you’ll find KANT Brewery, R'z Cafe, Iron Horse Saloon, and Zac's Diner all within walking distance. The Bullpen Suite blends comfort, convenience, and local charm.

FamilyValueCheck-in

Top Guest favourite

The interior of the cabin features a cozy living area with a plush sofa bed covered in a patterned quilt. A round area rug complements the wooden flooring, while a dining table with chairs is visible in the background, along with a small kitchen area equipped with essential appliances.

Cabin in Ferdinand

4.99 out of 5 average rating, 143 reviews

Eagle Pines Cabin (Eagle Adventures LLC)

Relax w/us at our beautiful, comfortable, and private Eagle Pines Cabin. We are 12 miles from Holiday World. The Cabin has its own private hot tub and also includes a private fire pit and we supply the firewood. Cabin is stocked with everything you’ll need. Hosts are on site, but out of sight. Our other rentals are Eagles Nest (3BR option) and Eagles Nest Plus (4BR option). Starting with the 2026 season check out will be at 10 am ON SUNDAYS ONLY, 11AM all other days.

ValueFamilySleep quality

Top Guest favourite

Cottage in Owensboro

4.97 out of 5 average rating, 434 reviews

Nature Lovers Retreat

This charming cottage is the perfect getaway for nature lovers. Relax in this home’s cheerful and cozy atmosphere, located on the edge of Ben Hawes Park with over 4 miles of beautiful walking trails and 7.5 miles of bike trails in this gorgeous 297 acre forest. Enjoy all the comforts of home, including free WiFi, TV, washer and dryer, full kitchen, and free parking. This special retreat is also only 1 mile from Ben Hawes Golf Course.

FamilyValueNearby

Top Guest favourite

A dining area is presented with a round wooden table and two upholstered chairs. A large wall-mounted television is positioned near a dark wooden console that holds decorative items. Natural light filters through sheer curtains, illuminating the warm-toned flooring.

Home in Newburgh

4.97 out of 5 average rating, 59 reviews

Walking The River

Just a short drive from Downtown Newburgh or the Eastside of Evansville, your family will be close to everything when you stay at this centrally-located place. Close to many local attractions like The Ford Center, University of Evansville, and University of Southern Indiana. It is also less than an hour's drive to Holiday World!

FamilyLocationQuiet