Holiday houses in Oakland City

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Top-rated holiday rentals in Oakland City

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

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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 out of 5 average rating, 52 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 favourite
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, 46 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 favourite
A gravel parking area is surrounded by lush trees, with a cabin visible in the background. Adirondack chairs are arranged around a fire pit in the foreground, creating a space for gathering. Bright blue skies with scattered clouds enhance the serene atmosphere.
Cabin in French Lick Township
4.99 out of 5 average rating, 234 reviews

Serenity Acres

Over 5 acres of pure serenity, just the sound of nature all around you! Beautiful Tucker Lake with hiking trail all around it just a mile away. This park like atmosphere has room for tents, RVs , boats, 4 wheelers and more. Just under 5 miles from the Fabulous French Lick and West Baden Resort town, but totally secluded.Cabin has two porches with rocker gliders and heavenly views. Cedar swing ,picnic table, fire pit with adirondack chairs for late night BBQs. Water park and boat rental, nearby

Top Guest favourite
The exterior of the Hobbit House features unique architectural elements, including curved rooflines and a distinctive round window. A manicured pathway leads to the front door, with greenery surrounding the entrance and decorative outdoor lighting providing subtle illumination.
Home in Evansville
4.97 out of 5 average rating, 116 reviews

Hobbit House 2 bedroom.

Welcome to the Hobbit House! Relax or work from home in this cozy house located in a charming, quiet neighborhood in central Evansville. Each room is curated to set a different vibe from relaxation, sophistication, and fun. This house also has an old speakeasy downstairs filled with arcade games and a movie projector and screen. At night relax in the backyard under a beautifully lit gazebo. This house is also equipped with an office set up to make it easy to work from your home away from home.

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, 419 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!

Guest favourite
Home in Evansville
5 out of 5 average rating, 9 reviews

Cozy Home 5 Mins from Airport + Free Parking

This spacious and comfortable home is perfect for families, groups, or business travelers looking for a relaxing stay. The house features 3 beautifully furnished bedrooms, including one with a king bed, one with a queen bed, and one with a full bed, offering plenty of space for everyone to rest comfortably. Enjoy a bright and cozy living area with 3 Smart TVs, perfect for relaxing after a long day. The fully equipped kitchen has everything you need to cook and feel at home during

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, 158 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 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, 64 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 favourite
The interior showcases a warm, wooden design with vaulted ceilings and exposed beams. A modern television is mounted on the wall above a stone fireplace, while a cozy seating area is arranged with a dark sofa and wooden coffee table. The space is well-lit and inviting.
Cabin in Corydon
4.97 out of 5 average rating, 128 reviews

The Geneva Cabin

The Geneva Cabin is one of a kind (not in the woods) and has everything you need to enjoy whatever occasion brings you to the area. Located less than 2 miles from the wildlife refuge, 10 min to downtown Henderson, 7 mi to I-69 the property sits in the middle of a quiet dead-end street. Right in the middle of anywhere anyway your journey takes you. 55” TV, sofa bed and recliner in living room, WIFI, washer & dryer. Fully equipped kitchen. Large parking area.

Top Guest favourite
Home in Chandler
5 out of 5 average rating, 22 reviews

City’s Edge II 2 Br/2 Ba K Q Laundry WIFI

Entire home in Evansville Area, 2 Bedrooms K Q, 2 Full Bathrooms-1 walk-in shower, 1 tub/shower, Washer Dryer, WIFI. Whether you are in town for business or pleasure this is a great location. This home offers privacy, convenience, and all of the essentials for short or extended stays. Smart TV in Living Room and Master Bedroom, WIFI included. Located 6 miles East of Evansville, IN 6 miles North of Newburgh, IN and 5 miles West of Boonville, IN.

Guest favourite
A small log cabin is nestled among tall trees on a wooded plot, accessible by a gravel path. Two black dogs are seen walking along the path, which leads to stone steps ascending to the cabin. The surrounding forest reflects greenery from spring foliage.
Cabin in Gentryville
4.94 out of 5 average rating, 159 reviews

The Cabin - Near Holiday World & Splashin' Safari

If you'd like a true log cabin feel while staying on a beautiful, serene wooded 10 acre plot of land, this is the place for you and your friends/family! This small cabin has been reconstructed after being transferred to this location by the owner and his son. All of the decor and fixings are antique in style to fit the log cabin feel, to bring you back to the good ole days.

Top Guest favourite
Cabin in Evansville
4.98 out of 5 average rating, 391 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

Popular amenities for Oakland City holiday rentals

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