Vacation rentals in Oakland City

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Top-rated vacation rentals in Oakland City

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

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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

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!

FamilyLocationKitchen

5.0 out of 5 average rating, 54 reviews

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

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.

ValueFamilyLayout

4.96 out of 5 average rating, 55 reviews

Guest favorite

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

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.

LocationAccuracyParking

5.0 out of 5 average rating, 9 reviews

Guest favorite

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

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.

LocationValueAccuracy

4.88 out of 5 average rating, 170 reviews

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

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.

LocationValueLaundry

4.97 out of 5 average rating, 73 reviews

Top guest favorite

A spacious game room features a red pool table alongside a round dining table. Bright lights illuminate the area, while a textured wall adds an element of depth. The room includes a seating area with benches and a few pieces of wall art, creating a relaxed atmosphere.

Home in Montgomery

Country escape with game room!

Very spacious with lots of space for the whole family to come and spend time together. Enjoy time by the fire in the unique patio grain bin, or in the basement game room playing board games, pool, or darts. Enjoy a meal in the large spacious kitchen with ample seating space for the whole family, 3 separate living areas with smart tvs. 4 full baths, Bedrooms include 2 king beds, 3 queens and possibly 3 or 4 twin beds in the basement game room storage area.

LocationFamilyBackyard

5.0 out of 5 average rating, 26 reviews

Superhost

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

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

FamilyLocationCondition

4.87 out of 5 average rating, 313 reviews

Top guest favorite

Cabin in West Salem

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.

FamilyValueCondition

4.99 out of 5 average rating, 170 reviews

Superhost

An indoor pool area features a long, narrow pool, surrounded by large windows that allow natural light to fill the space. The tiled floor is complemented by potted plants, and wicker chairs with cushions are arranged nearby for seating.

Vacation home in Evansville

Nugent House

It's rare to find a place that's both historic and one-of-a-kind. Whole house to enjoy in downtown Evansville Indiana. Walking distance to arts district , bars , restaurants, casino , ford center , Evansville museum, Evansville riverfront and much more.,, Home was built in 1915 as a mansion by the Nugent family. No lifeguard on duty, swim at your own risk

FamilyValueAir conditioning

4.93 out of 5 average rating, 217 reviews

Top guest favorite

A two-story farmhouse is set in a tranquil rural landscape, with a blend of modern renovations and vintage charm. The exterior showcases a gray facade and red brick accents, framed by open fields and trimmed grass. Leafless trees provide an interesting contrast around the home.

Farm stay in Ferdinand

Wilmes Farmhouse

Enjoy a getaway to the serene environment of the country in this secluded location that is also only 10 minutes away from Holiday World. The renovated home has modern amenities while retaining the charm of a vintage farmhouse. Just added fiber internet and it works great.

LocationFamilyGrill

4.92 out of 5 average rating, 189 reviews

Guest favorite

Home in Mount Carmel

Comforts Of Home

Our home is a peaceful and centrally-located place, on historic N Market Street just a few blocks from Uptown Mt Carmel, and 2 blocks from Wabash General Hospital, and assisted living facilities. We are just a few blocks away from resturants and shopping.

LocationFamilyKitchen

4.96 out of 5 average rating, 50 reviews

Guest favorite

Home in Evansville

Country Homeplace Pool/By Toyota/Sleep 14/Pets Ok

I run this property for my mom who has moved to Hawaii . Our housekeeper & son live in the attached mother in law suite but do not share any space with you . You may see her or her son outside on occasion .

LocationFamilyBathroom

4.87 out of 5 average rating, 23 reviews