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.

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.

Southern IN Retreat Near Spring Mill & Lake Monroe

✨ ADA Accessible luxurious hideaway in picturesque Southern Indiana. Nestled in charming Bedford—at the heart of picturesque Lawrence County—Q Street Bungalow invites you to unwind in timeless elegance and modern comfort. This beautifully appointed, single-story retreat is fully wheelchair-accessible with a permanent ramp, ensuring ease and comfort for every guest. Parents will also appreciate many essentials for convenient traveling with toddlers, including a crib, highchair, etc.

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.

Pleasant View Lodge

Pleasant View Lodge is a great country get away, relaxing front porch with rocking chairs and beautiful views and great hiking areas . Our farm has easy access with a blacktop drive way and plenty of parking, 3 miles from U.S.Hwy 50 east of Bedford. Our modern one story house features 2 bedrooms, 2 bathrooms and an open concept living area and kitchen plus a garage. No children under the age of 12 and no pets are allowed.

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.

Cedar Crest Cottage

Relax with the whole family at Cedar Crest Cottage. Peaceful country setting away from the city but close enough to explore Bedford, Mitchell, and Bloomington Indiana and other places in the area. Close to beautiful Monroe Lake and Springville state park. House has all you need for an extended stay. Washer and dryer, pots and pans and every amenity to call it home for your get away. Book your stay today!

Timeless Retreat

The whole group will be comfortable in this spacious and updated home! Historic charm with modern comforts right in the heart of Bedford. Just a few blocks to downtown. The Milwaukee Trail is 1 mile away ! Indiana University is just 25 miles! Lake Monroe is 18 miles. French Lick Casino is a 40 minute drive!