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.

Marilyn's Cottage-Park Setting, King Bed, Fire Pit

Hidden gem! This getaway features 2Bd/2Ba and an open loft bedroom. Master retreat is on the main floor. Huge family room and dining for 6. Relax by the fire pit or grab a cup of coffee and enjoy rocking on the covered front porch. Location is easily accessible to Bedford, Bloomington (IU Football & Basketball), NSWC Crane, Lake Monroe, Spring Mill and Brown County State Parks, and Bluespring Cavern Park. 15 minutes to major restaurants and 2 miles from Dollar General. Nature lover's dream!

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.

Vintage 1920s Bungalow

1920s Vintage Bungalow: Cozy retreat, easy access to 37 & 50. 20 minutes to Bloomington and Indiana University, Lake Monroe. Renovated arts and crafts cottage perfect for family getaways, IU reunions, girlfriend getaways, scholars, writers, artists . Comfortably sleeps 4 adults. Full laundry, great double lot yard & gardens, cozy front porch and patio for relaxing. One block from entrance to Old Milwaukee RR hiking and pet walking trail. Fully equipped kitchen. Great family neighborhood.

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.

Lakeside Cabin | Serene Lake Monroe Views + Deck

Discover serenity at the Lakeside Cabin—an elevated retreat overlooking Lake Monroe. Fully renovated in 2023 and designed by Fleck Home, it offers calming interiors with modern comforts while connecting you to the outdoors. Enjoy a wraparound deck, fire pit, outdoor grill, fully stocked kitchen, luxury bath, and thoughtful sleep touches like a Snooz sound machine and multiple pillow styles. Whether you’re seeking a peaceful escape or a lakeside adventure, this cabin delivers it all.

Modern home close to Bedford & Bloomington.

Kick back and relax in this new & stylish space. Completely remodeled with all new furnishings & appliances. A large back deck overlooking a large backyard. Is in a country setting but close to highway 37 & I69. Three miles to Lake Monroe, 1/2 mile to Dollar Store & local gas stations, 7 miles to Bedford & 13 miles to downtown Bloomington. 3 miles to stone crest golf course & The Point. Owners are close to property in the event you would need anything. FOUR guest maximum.

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.