Vacation rentals in Oolitic

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 private, wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances complete seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridgetop retreat.

Cozy & Unique a Readers Retreat | Downtown Loft

Welcome to your Library Loft in Downtown Bedford, a warm, character filled escape designed for relaxation and inspiration. Located on the 2nd floor, this unique stay features a stunning built in library, creating a cozy space perfect for reading and unwinding. Thoughtfully designed with comfort and charm, it offers a one of a kind experience just steps from downtown shops, dining, and a short drive to Bloomington. This stay offers a one-of-a-kind experience you won’t find anywhere else in town.

Cheerful two bedroom Farmhouse with free parking

Your family will be located in a lovely Bloomington rural setting that is less than 10 miles from Indiana University and less than 5 miles from beautiful 10,750 acre Lake Monroe. You will be able to unwind on the front porch swing, relax on the spacious back deck or warm your hands and feet by the fire pit provided. If you are a foody you are within 10 to 15 minutes from the many Bloomington restaurants or if you prefer the cooking option there is a full kitchen for your culinary creativity.

Barn stay @ Goose Creek Chalet

This unique barn/log cabin was constructed by a creative craftsman Tom Kirkman. This home has been published in a book " From White House to Amish." The property has two separate lofts. The south loft has a master bedroom with French doors leading to a soaker tub and shower. The north side loft has two bedrooms with queen size beds and one bedroom with two full size beds. The main floor has 30' cathedral ceilings, freestanding fireplace suspended on chains, 16' dining table, custom kitchen.

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.

Cozy, Quaint, & Newly Renovated!

WELCOME HOME to your ONE bedroom, ONE bathroom ranch! This home has been newly RENOVATED from the ground up. Step inside to be greeted by your cozy sunroom that flows right into your open concept living room and kitchen. Kitchen is spacious offering plenty of room to cook. Down the hall you will find your master suite with access to the full bathroom that also is accessible to your stackable washer and dryer area. The side door opens to a patio perfect for grilling and yard space to relax.

Treehouse Retreat With a View of National Forest

IU Fans! This quaint apartment home is about five miles east of Bloomington and the IU Campus on Hwy 446. The property borders Hoosier National Forest and adjoins 8 miles of hiking trails, with just a short trek to Lake Monroe and a mile to Paynetown SRA. The living room has a wall of windows that looks out over the woods. A bright and airy kitchen w/ all major appliances is off of the living room. An interesting bedroom with a dormer and a large bathroom/ laundry room complete the home.

The Little White House

2 BR-1 BA-1 Sleeper Sofa. Sleeps 6 Freshly renovated and charming 1920, 2 bedroom 1 bath home with screened in back porch and a private, fenced in back yard. Easy access to hwy 37, I-69, and is located just off hwy 58 (5th St). 5 blocks to the Milwaukee Walking/Biking Trail. Close to many shops, restaurants, pubs, and grocery stores. 10 miles to Lake Monroe, 21 miles to Bloomington (28 to IU), 21 miles to Oliver Winery, 29 miles to French Lick and West Baden Resorts/French Lick Casino.

Home away from home

Enjoy this charming 2 bedroom 1 bath stylish home thats centrally-located in a quiet area that offers a nice front deck and cover back patio. 2 blocks from the Milwaukee Trail Centrally located near parks & restaurants. 25 miles to Indiana University 15 miles to Lake Monroe and the Hoosier National Forest. 15 minutes to Spring Mill State Park. 35 miles to French lick Casino There’s a long driveway on the right side of the house as well as street parking.

Red Cedar Log Cabin | Romantic + Hot Tub

Cozy, secluded, and full of charm, Red Cedar Log Cabin is the perfect Brown County getaway for couples. Soak in the private hot tub, unwind by the wood-burning fireplace, and enjoy the peaceful wooded setting. With rustic character, modern comforts, and easy access to Nashville, trails, shops, and local dining, this cabin is made for quiet mornings, cozy nights, and unforgettable weekend escapes. Book your stay and experience Brown County at its coziest.

Harmony Hills 3 bedroom farm house

This 1970s brick farmhouse on 60 acres of pasture, forest, and stream offers a cozy “grandma’s house” vibe. Enjoy 3 beds, plus pullout sofa, 2 baths, and a basement with washer/dryer. Brick walls keep it quiet despite nearby highway noise. Outside, a roofed deck with grill and a campfire ring with firewood await, lit by string lights for cozy nights. Just 20 min from IU, it’s a serene escape for families or nature lovers.

The Edge

Unique, peaceful, modern and cozy A-frame cabin. This private cabin is just minutes from Bloomington and the lovely IU campus, Go Hoosiers! Nature views from all windows and private deck with bbq grill and seating for 6. Features include 2.5 acre wooded lot and an overlook at the edge of the creek. Also a firepit, deck, front porch, and hiking trail make this great for a couples or parents' retreat or game events.