Vacation rentals in Medora

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Top-rated vacation rentals in Medora

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

The two-story log cabin is nestled among trees, featuring a front porch with two rocking chairs. A grassy area surrounds the cabin, complemented by wooden lattice details along the base and large windows that invite natural light.

Cabin in Bedford

Schitt’s Cabin

Experience the novelty and delight of rural living in a charming log cabin on a hill in the forest. Nicknamed “Schitt’s Cabin” because of the charm and Schitt’s Creek references, “The Cabin” is your favorite cabin away from home. As in Episode 5, Season 1 of Schitt’s Creek, you’ll be surprised in more ways than one by our charm and you’ll have the entire place to yourself— inside and out! The cabin is nestled on 6 acres of forests and sits remote atop a hill. Cell phone signal here is spotty.

4.85 out of 5 average rating, 73 reviews

Top guest favorite

Train in Spencer

Eagle Ranch Railway Retreat

All aboard! Stay in our historic red caboose turned tiny home at Eagle Ranch. Nestled by lakes and farmland, it’s the perfect spot for unplugging from city life and enjoy some fishing, kayaking, swimming, roasting smores on the fire, and stargazing in the hot tub. Inside you can relax by reading in the library, playing games, or streaming tv. The caboose has a pull-out queen sofa bed that fits the cozy layout. It's truly a unique stay where nature, history, and adventure meet! (18+ recommended)

4.91 out of 5 average rating, 81 reviews

Top guest favorite

A modern cabin features a large deck surrounded by lush greenery, showcasing expansive glass windows that provide ample natural light. The structure has a sloped roof and is partially nestled among tall trees, highlighting the serene forest setting.

Cabin in New Pekin

Anjuna House - a Scandi riverfront forest getaway

Welcome to the enchanting retreat of "Anjuna," nestled among a sprawling forest in the heart of southern Indiana. This modern 4-bedroom, 3 bathroom luxury cabin features 14' floor-to-ceiling windows, and 1000+ sqft deck! Outside there are 12 acres of forest to explore, an outdoor shower and a tranquil river which meanders through the property. Anjuna is near Knobstone trail, Marengo Cave, and the bourbon trail in Louisville. Bring family, friends or just yourself to relax or explore at Anjuna!

4.97 out of 5 average rating, 115 reviews

Guest favorite

A serene cabin is nestled among lush green trees, featuring a sloped roof and large front windows. The welcoming front porch is flanked by a gravel pathway, leading to an entry door. A wooden fence encloses the property, enhancing the sense of privacy.

Home in Vallonia

Hollow Creek Getaway

Relax with the whole family at this peaceful, secluded location. Enjoy access to over 2,000 acres of public land with hiking trails, mountain bike trails, scenic views, kayaking, fishing & hunting (in season). The cabin offers 3 bedrooms with 2 full bathrooms and 2 living areas on separate levels. Air hockey, fooseball indoors; front porch and back patio with grill and outdoor seating. Fire pit area for bonfires. Creek to fish and play in. Private setting with cabin 1/4 mile off the road.

4.95 out of 5 average rating, 73 reviews

Top guest favorite

A charming cabin exterior is showcased with a green metal roof and wooden log siding. Soft lighting highlights the entrance, adorned with nature-inspired decorations and plants. The paved driveway leads to the front door, creating an inviting approach amidst the natural surroundings.

Cabin in Salem

Fox Den Retreat Cabin

No PETS ALLOWED of any Kind, relax in peace, at this unique and tranquil getaway. nature abounds with the flight of Hummingbirds, Butterflies, Birds and the peaceful and tranquil ambiance of a remote nature cabin. with plenty of places and things to do within 5 to 30 minutes of the cabin. Hike the Knob Stone trail all the way to Kentucky. Parks, Speedway, Drag Strip, Golf at Western Hills golf club. swim, Boat, fish at Delaney Park 5 minutes away, 10 minutes to Starve Hollow State Park.

5.0 out of 5 average rating, 30 reviews

Top guest favorite

Cabin in Unionville

IU vs Purdue Game Day Cabin Getaway

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances 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 ridge top retreat.

5.0 out of 5 average rating, 220 reviews

Top guest favorite

A two-story red barn-style structure is set amidst a wooded landscape. The building features large windows, allowing natural light to brighten its interior. A driveway is visible leading to a spacious garage door, with gravel and greenery surrounding the entrance.

Barn in Salem

Heart Of the Woods in Salem with Private Lake

Welcome to your tranquil escape! Nestled on a 91-acre wooded property with an 11-acre lake, this apartment is more than just a place to rest your head - it's a retreat for your mind, body, and soul! As you arrive, the wooded driveway welcomes you, often dotted with scampering squirrels and glimpses of deer, setting the tone for a peaceful, nature-rich stay. The 1150 square foot apartment is both spacious and cozy, thoughtfully designed to feel like a true home away from home.

5.0 out of 5 average rating, 27 reviews

Top guest favorite

Home in Freetown

Retreat on Salt Creek

Relax with the whole family at this brand-new structure with attached two car garage in a peaceful country setting. Enjoy spectacular sun rises and sets on the expansive covered front and rear porches. Situated on 2.25 acres with Salt Creek running through the property ready to be explored, bringing nature to your back door. Just minutes from Brown County located just a mile off of State Road 135 this property is a five-minute drive to the Salt Creek Winery.

5.0 out of 5 average rating, 18 reviews

Guest favorite

A modern home is positioned on a hillside, featuring a sleek black exterior and large windows that allow for ample natural light. A balcony extends from the structure, providing outdoor seating and a view of the surrounding trees.

Cabin in Nashville

Modern Nashville Home in the Woods

Welcome to Plāhaus — a modern retreat tucked into the woods of Brown County. #1 Most-wishlisted Airbnb in Indiana per Airbnb Designed for solitude, relaxation, and connection with nature, Plāhaus blends modern architecture with peaceful surroundings. Take in the views from the balcony, gather around the firepit, or explore nearby Nashville’s shops and restaurants. Perfect for romantic getaways, family escapes, or simply recharging from everyday life.

4.99 out of 5 average rating, 534 reviews

Top guest favorite

An outdoor fire pit area features six black Adirondack chairs arranged around a central fire pit. The setting includes a backdrop of gently rolling hills and a covered porch area, illuminated by warm evening light under a colorful sky at sunset.

Home in Vallonia

3BR/3BA Peaceful Retreat - Fire pit & Game room

HIGHLIGHTS: Cozy Indoor Fireplace Fire pit and outdoor seating/porch swing Fully stocked kitchen High-speed Wi-Fi and smart TVs Infinity game table Washer and Dryer 3 Full bathrooms Escape to serenity at this barndominium nestled in rolling hills, woods, and open fields in the heart of southern Indiana. This modern retreat offers the perfect getaway for families, couples, or small groups seeking privacy and adventure.

4.97 out of 5 average rating, 32 reviews

Top guest favorite

A private deck is furnished with two wicker chairs, each with purple cushions. The surrounding landscape features a lush green lawn and several trees, creating a serene outdoor space. Clear blue skies complete the tranquil setting.

Home in Bedford

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!

4.98 out of 5 average rating, 129 reviews

Top guest favorite

A spacious living area features a vibrant blue tufted sofa, complemented by a decorative area rug and wooden coffee table. Natural light enters through large windows, illuminating the open design that connects to a kitchen area in the background.

Apartment in Seymour

Stay above a coffee shop @ The Urban Perk!

This stylish place to stay is perfect for group trips. Centrally located in the commercial historic district with a coffee shop downstairs! This apartment is walking distance from shops and restaurants downtown. The building was renovated in 2022, but the historic charm remains!

5.0 out of 5 average rating, 150 reviews