Vacation rentals in Oakland City

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakland City

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

1 of 1 pages1 / 1
Top guest favorite
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 out of 5 average rating, 51 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!

Top guest favorite
A dining area is showcased with a wooden table surrounded by six chairs. A buffet table is positioned against the wall, displaying items for coffee. Natural light filters through a window adorned with light curtains, illuminating the tile floor.
Home in Evansville
4.96 out of 5 average rating, 45 reviews

Rolling Meadows Place

This well maintained, newly decorated home is in a quiet subdivision yet close to restaurants/attractions. Its generous sized well-equipped kitchen will help make mealtimes special. Three cozy bedrooms all with smart TV’s, a washer/dryer and large living room with a 65” smart TV will make you feel at home. Self check-in and a two-car garage with the driveway make getting settled a snap. The business person has a dedicated, well stocked spacious desk, comfy chair, high-speed Wi-Fi and printer.

Top guest favorite
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, 167 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.

Top guest favorite
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, 412 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!

Top guest favorite
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, 47 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.

Superhost
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, 152 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.

Guest favorite
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, 61 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.

Top guest favorite
An outdoor deck features a rectangular table with a central hole for an umbrella, surrounded by four wicker chairs. Lush greenery and trees provide a natural backdrop, with a peaceful lake visible in the distance.
Cottage in Huntingburg
4.88 out of 5 average rating, 287 reviews

Lakeside Cottage Getaway Fishing, Hiking, Relaxing

Enjoy the lovely setting of this romantic spot in nature. This quiet getaway comes with a full kitchen, two bedrooms, access to a lovely lake, and an outdoor deck for enjoying the view. The master bedroom has a queen size bed and a crib. The second bedroom has a twin bed and a bunk bed [twin over full]. This space is perfect for singles, couples, or even large families. Close to Patoka Lake and Holiday World. No smoking/not handicap accessible

Superhost
The property is surrounded by tall trees, providing a natural setting. The cabin features a unique architectural design with circular windows and a sloped roof, partially obscured by foliage. Leaves cover the ground, indicating the changing season.
Cabin in Loogootee
4.82 out of 5 average rating, 122 reviews

Peaceful Lake House Cabin 1, Direct Water Access!

This Cozy Cabin Duplex is located directly on West Boggs Lake, with a large, wrap-around, stationary dock to fish from, and multiple floating docks for your boat! Enjoy our kayaks, free with your stay, and explore all West Boggs has to offer! Cabin features 2 bedrooms with 2 Queen beds and a pull out sofa bed in the living room. Fully equipped kitchen, full bathroom, and an amazing deck for watching the sun set.

Top guest favorite
The cabin's exterior is gently nestled among lush greenery, showcasing wood siding and a welcoming red front door. A paved pathway leads through manicured landscaping, with trees providing shade in the vicinity. The serene lake is visible behind the cabin, enhancing the natural setting.
Cabin in West Salem
4.99 out of 5 average rating, 160 reviews

Lake Cabin in the Woods

🌲Escape to peace and nature at Lake Cabin in the Woods! Unwind in your private hot tub, enjoy the shared pool, and soak up year-round tranquility surrounded by trees and wildlife. Located between I-70 and I-64, about 60 miles from Effingham, IL and Evansville, IN, our cozy cabin offers the perfect blend of seclusion and convenience—ideal for relaxing, recharging, and reconnecting with nature.

Top guest favorite
Cabin in Evansville
4.98 out of 5 average rating, 385 reviews

Nama-Stay ~ A Zen Cabin Retreat

Rustic and cozy cabin nestled in the middle of 3 wooded acres. It provides the perfect escape for travelers looking for a peaceful, quiet getaway, with modern amenities. Conveniently located ten minutes from downtown. House Rules • No Pets • No Smoking • No Parties • No Weddings, Events or Commercial Use • Must be 21 to book

Top guest favorite
Home in Lewisport
5 out of 5 average rating, 9 reviews

Cozy, convenient, golf!

Great for a vacation or work stay, this 4 bedroom 3 bath house sits 50 yards from the golf course. A secluded private drive gives a great view including a front and back covered porch . All the amenities of your house including a full kitchen, large screen tv with high speed internet, fireplace, and a golf cart!

Popular amenities for Oakland City vacation rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Gibson County
  5. Oakland City