Holiday rentals in Medora

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Top-rated holiday rentals in Medora

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

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Top guest favourite
Cabin in Unionville
5 out of 5 average rating, 209 reviews

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.

Guest favourite
The living room features a spacious layout with a futon couch and two sitting chairs arranged around a coffee table. Exposed wooden beams and warm lighting enhance the cabin's rustic charm. A fireplace insert is visible, contributing to a cozy atmosphere within.
Cabin in Nashville
4.98 out of 5 average rating, 171 reviews

Brown County Woods - Cabin 2 king beds Secluded

If you like to be close to everything in Nashville, IN while being in the middle of the woods, this is the place for you. This Cabin is about 2,500 feet from the main road and feels like the middle of the woods. Additionally, Brown County State Park is directly next to the west and north property line boundary. The property is 24 acres total, about 20 acres of mature woods. In just over 5 minutes, you can be to the north entrance of Brown County State Park or in downtown Nashville, Indiana.

Top guest favourite
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
4.96 out of 5 average rating, 106 reviews

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!

Guest favourite
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
4.94 out of 5 average rating, 64 reviews

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.

Top guest favourite
The exterior of the estate features a charming porch adorned with potted plants and a flag. Sunlight filters through the surrounding trees, illuminating the stone and wood structure. A stone pathway leads through the lush green lawn, enhancing the inviting outdoor space.
Cabin in Henryville
4.97 out of 5 average rating, 379 reviews

Close to Louisville~Hot Tub~Fire Pit~Game Room

Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full kitchen, laundry, and office. Guests will have full use of the grounds including the hot tub, fire pit, and the numerous covered decks & patios. Perfect romantic getaway or multi person retreat.

Top guest favourite
The entrance to the cabin features a covered porch with rustic wooden supports and decorative string lights. A welcoming outdoor seating area is visible in the background, surrounded by lush greenery and shaded by nearby trees. The path is lined with stones and small plants.
Cabin in Unionville
5 out of 5 average rating, 504 reviews

Cozy Cabin Close to University 1

The Red Rabbit Inn is located just 15 mins from the Indiana University campus and just 20 mins from Nashville, IN , this architecturally designed cabin features the works of local artisans. Beautifully landscaped on a secluded, wooded pond, this cabin includes a loft bedroom with KING bed, bath, full kitchen, gas fireplace, TV & Wifi, with your own private deck, outdoor hot tub, fire pit area & gas grill. Cabin sleeps 2 guests. Located near Lake Lemon, in a beautiful serene setting.

Top guest favourite
Guest house in Hardinsburg
4.96 out of 5 average rating, 360 reviews

Little Cabin in the Woods - Bent not Broken

Discover your next FAVORITE place to visit. Welcome to Always Ranch LLC where this unique, tiny cabin offers you a tranquil spot to relax and unwind. You will be surrounded by nature as we live on a horse ranch. The cabin may look crooked, but the inside it is rustic and warming. See our Guide Book for close by suggestions. We aren't too far away from local attractions. The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill.

Top guest favourite
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
5 out of 5 average rating, 23 reviews

Heart Of the Woods in Salem

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.

Top guest favourite
The exterior of the cabin showcases a rustic log structure with a green metal roof, surrounded by lush greenery. Two wooden rocking chairs with colorful cushions are positioned on the porch, inviting relaxation. Large windows provide a glimpse of the peaceful woodland setting.
Cabin in Nashville
4.96 out of 5 average rating, 125 reviews

Red Cedar Log Cabin | Hot Tub! + Pet-Friendly!

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.

Guest favourite
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
5 out of 5 average rating, 523 reviews

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.

Top guest favourite
The exterior of the modern home is shown, featuring a blue-gray facade with a sloped metal roof. A spacious wrap-around porch contains orange seating and large windows, surrounded by lush green grass and trees, providing a serene wooded setting.
Home in Bloomington
4.98 out of 5 average rating, 445 reviews

Bloomington Lake-View home on 40 secluded acres

New Lake home that sits on 40 acres of woods with gorgeous views. Large wrap around porch with outdoor seating and chill space. Fall, winter and spring provide amazing views of Lake Monroe. While summer allows for easy access to Lake Monroe. Plenty of room to park a boat or have multiple cars. The home has modern decor with wood stove, new appliances, surround sound and all of the amenities you need for your stay. Just 20 minutes from IU.

Top guest favourite
The mid-century modern house is surrounded by lush greenery, featuring large windows that invite natural light. A spacious back deck with bright orange chairs is visible, providing a cozy spot to enjoy the outdoors.
Home in Nashville
4.97 out of 5 average rating, 233 reviews

Nashville Treasure

This mid-century modern one bedroom house is located just 15 minutes from historic Nashville. Beautifully decorated and adjacent to Yellowwood State Forest. This house has an open floor plan. The large kitchen is open to a large family room. You can lounge in comfort or sit on the back deck and watch the wildlife. Newly remodeled in 2019 it is a sight to see. You will be making plans for your next visit.

Popular amenities for Medora holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Jackson County
  5. Medora