Holiday rentals in Oaktown

Sunroom & Huge Sectional • 5 Min IU • Relax

A spotless, thoughtfully curated home designed to feel comfortable, calm, and genuinely livable — not a bare rental. Guests consistently mention the immaculate cleanliness, comfortable beds, oversized sectional, and thoughtful extras that make settling in easy. Located in a residential neighborhood, under 10 mins to IU, downtown, stadiums, dining, parks, and Kroger. This home is ideal for campus visits, couples, small groups, and professionals who value comfort, cleanliness, and a calm place.

Family Getaway w/ Spacious Yard

This peaceful place to stay is perfect for group trips. It is located just 50 yards from the Elnora Bible Institute. If you have a family gathering at the school, it is nice to be close to the party, but have your own space. It features a campfire seating area for special times with family and friends. A swing set for the children, a large yard for games, outdoor lighting, and a Weber grill, makes it a perfect place for a get-together. The kitchen is stocked and ready for you to prepare meals.

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.

River Rock Cabin

Come to beautiful southern Indiana and stay in our rustic cabin with all the comforts of home. Overlooks White River, close to Bedford, Bloomington, near Spring Mill Park & Bluespring Caverns. There is hiking nearby at Hoosier NF and Milwaukee Trail. Great home base if you are going to IU football game, French Lick or just want to get away for a relaxing weekend. Lots of golfing near by. Limestone bluff overlooks the White River 125 ft. below cabin porch. There is a patio plus a fire pit.

Maria’s Haven

Welcome to “Maria’s Haven”💕 A beautiful cozy home in the heart of a beautiful small town. This home belonged to my mother, Maria, who passed away in 2020 to breast cancer. This home was truly her “Haven”. Take a walk to the local diner, museum, Gosport playground, local shops, or to our delicious Amish bakery. We are also just a few miles from the popular “Hilltop” restaurant as well as McCormicks Creek State Park. Our mission is to make you feel like you never even left home. ☺️

The Rustic Retreat

Enjoy your stay at the Rustic Retreat. The large living room offers plenty of space for work or relaxation. Has washer/dryer. The back yard offers a grill, picnic table, extra chairs and umbrella. Roku TV and Wi-fi available. Full size bath with shower, King and Queen beds, with additional TV in the King room. The kitchen has many items for your cooking needs. Off street parking and close to many amenities. Dusk-to-Dawn light that shines over the back yard and driveway.

Sweet Dreams Cabin. Peaceful & Relaxing

Get some quality family time at this newly remodeled cabin near the beautiful Embarrass river. You are surrounded by beautiful woods and a small creek. Lush wildlife is all around you so you can be one with nature. The cabin has all the luxury's to allow for a long term stay as well. Beautiful Lake Charleston is not far away. The large circle drive offers plenty of parking for your boat and guest. The large deck on the rear gives a beautiful view to be enjoyed by all.

Lake Harvey Vacation Rentals - 2-Bedroom Bungalow

Relax in our 2-bedroom Bungalow on 15-acre Lake Harvey just south of Linton, Indiana on the edge of Goose Pond Fish & Wildlife area, and just minutes from Greene Sullivan State Forest. Perfect for your hunting/fishing trip, or to bring your family for a peaceful vacation. Our Bungalow features 2 bedrooms, one with 2 queen beds, and one with a double bed, living room, dining room, fully equipped kitchen, 2 full bathrooms, and an attached carport.

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.

Barndominium studio with private yard & Hot tub

The Barndominium is a beautiful example of an industrial loft style apartment with an open concept high ceiling features a full kitchen / laundry and private bathroom situated in a private area creating a feeling of being surrounded by forest while still being close and convenient to IU and Lake Monroe ! check us out on Instagram @btownbarndo

Airy apartment, beautiful view

Enjoy our bright, spacious, well-furnished 1-bedroom apartment for your visit to Bloomington. This very private space is in the beautiful countryside on the west side of Bloomington, conveniently just 15 minutes from campus and only 5 miles west of 37. The view from every window is beautiful, allowing for a very relaxing stay.

The Getaway House

Welcome to our Get Away House. Located on the edge of Loogootee, it is a very peaceful area and yet close to the local stores and restaurants. Relax with the family and spend the evening on the back patio. With two bedrooms and one bathroom, this single level home is perfect for your night away.