Vacation rentals in Oakland City

Comfy house on outskirts of town.

Fully stocked house for 4 clean linens, blankets, dishes, shampoo, conditioner, soap, vacuum, iron/board Has 2 electic bikes with a places to ride, eat, and drink within minutes. Has comfy recliner couch and 2 chairs, 50" smart tv, and a dvd player in Living room. Outdoor table and chairs 2 bedrooms, 1 queen bed main level, 1 full size, upstairs, a extra air up matress and blankets in closet if needed. Parking for 2 vechicles. Ask to see if we can accommodate trailers and bigger vechicles.

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.

New Harmony Cottage

Open concept cottage w lots of space for one or two located in the Historic District of New Harmony. Free street parking, a sitting area and comfortable queen bed. Washer/Dryer and a small kitchenette (no stove or cooktop.) WiFi and and a Smart TV for your convenience. Bring your Netflix or Hulu passwords. Be our guest in your own space. Easy no contact checkin & checkout. Coffee/Tea bar or Black Lodge Coffee! *FYI check hours for shops & restaurants that you plan on visiting.

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.

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.

Lake Cabin in the Woods

🌲Looking for a relaxing getaway? Need a peaceful stopover on your Midwestern travels? Craving tranquility in a remote setting? Look no further—Lake Cabin in the Woods is your perfect retreat! Nestled about 60 miles from both Effingham, IL and Evansville, IN, our cabin offers the solitude you’re seeking without being too far from major highways. Located between Interstate 70 and Interstate 64, it’s a serene escape with easy access to wherever your journey leads.

Cunningham Cottage

The Cunningham Cottage is a 2 bedroom, 1 bathroom, home nestled in the heart of Mt. Carmel, IL. This newly-updated cottage features a spacious walk-in shower and double vanity, two queen-size beds, a covered garage, screened in patio and so much classic charm. Enjoy the convenience of a washer and dryer, local coffee shops, boutiques, restaurants and other small businesses within walking distance.

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. 2 complimentary drip coffees are included with your stay.

City’s Edge, 3 Bed (K,Q,T) 2 Full Bath, Laundry

Located 6 miles East of Evansville, 6 miles North of Newburgh and 5 miles West of Boonville. Whether you are in town for business or pleasure this is a great location. You are sure to find anything you need in a short driving distance. Home has 3 bedrooms 2 full baths. Smart TV in Living Room and Master Bedroom. WIFI included.