Vacation rentals in Trimble County

The Row House

Modern flair with antique charm sets this BnB apart! Located on quiet street in the heart of historic downtown Madison, this fully renovated 1830s Row House has you steps away from everything! Whether it's a festival or fall colors, a boat race or car show on the riverfront, a micro brewery or winery, antiquing or historic tour, hiking Clifty Falls or simply just getting away, we have the location for you. *HVAC system includes whole-house air purifier. Max of 4 guests, no children under age 8.

Stablemaster’s Quarters/ Best downtown location!

Come see why the city awarded us with the “Stellar Award”, Best Place To Stay in Madison! The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, laundry room & a furnished white kitchen will all be appreciated. Yet, historic charm remains. You will soon see why the entire building has won multiple awards. Come see why US Today awarded Madison “ Best Small Town in the Midwest”.

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 180 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

Historic Madison Spa Retreat perfect location

Highlighted on Madison Loft Tours. 1800s historic 3rd story charming Loft offers a spa retreat & private deck. In the midst of Madison’s shopping, dining, festivals & nightlife. Located between Main St and the river. Antique furnishings and beautiful woodwork highlighted. Sip local coffee from our private deck or relax in a jacuzzi tub after touring the sights. Wineries, bars, Mad Paddle Brewery and great restaurants surround us. Hanover College & Clifty Park are minutes away.

Riverview Historical Retreat

Full time Airbnb home in Historic Downtown Madison. This two bed, two bath home overlooks the Ohio River and includes a fully stocked kitchen, washer/dryer, screened in back porch, internet, keyless entry, and more Centrally located next to Bicentennial Park, enjoy one of the many restaurants, bars, parks, and local events, or enjoy a quiet weekend away with a weekly Music/Movie by the river, a local farmers market, and shops. There is something for everyone to enjoy in Madison

Running Creek Log Cabin

Our cabin is about 6 miles to dock your boat onto the Ohio River. A 15 minute drive into downtown Lagrange for more shopping including food and boutiques. We are 30 drive into Louisville and 1 hour 15 min. drive to Cincinnati Ohio. It is on a 5 acre property and attached by a driveway to a home that we call Southwest Retreat that is on airbnb and 5 acres. We have a security camera on the outside of the house on the front porch facing the driveway.

T&E Riverhouse Retreat

Wake up to the Ohio River stretching endlessly beyond your windows. Sip coffee as barges drift by. End your evening under the stars beside the firepit. Whether you're here for a peaceful getaway or an action-packed vacation, the TE Riverhouse Retreat has everything you need for an unforgettable experience. Book your stay today and create lasting memories. The home features upper/lower decks, a basketball goal, a fire pit, and a kitchen on each level.

Tiny Home in Amish Country

Our Tiny Home sits on our farm called, Tenacity. It is a separate home attached to our home by a wrap around porch. The Tiny House is 800 sqft located on 70 rolling acres of north central Kentucky. This farm has a rhythm that will slow your heart rate, clear your lungs, and revive your spirit. Fireflies light your summer evening under the night sky. Amish families in their black buggies smile and greet you as you pass them on the road. LGBTQ+safe zone

Fossil Creek Woodlands...Rustic, Private, Retreat

Fossil Creek provides a rustic relaxing environment for family and friends to escape the hustle and bustle of every day life and enjoy beautiful Kentucky woodlands. Our home is situated at the base of 65 wooded acres in Oldham County Kentucky. Its name comes from the plethora of fossils that can be seen in the creek that runs along the front of the property. Our place is great for couples, families, reunions, retreats and church groups.

Little Lamb Retreat at the river

Just Minutes to Belterra!!! Hunters welcome we have 7.5 acres. Relax with the whole family at this peaceful home. Or have a romantic get away for 2. Spacious and beautiful home with awsome views. Centrally located (within 20 minutes) to historic Madison and close to Beltarra casino and resort. Come and enjoy a few days away, a week or a as long as you want! Come and enjoy!!! FYI- IF bringing pets they must be on the reservation!!!

The Crafty Fox Den - Retreat House

Nestled in Madison, Indiana’s beautiful historic district. The home is a newly renovated four square craftsman, located in the middle of town, still quiet and cozy. You are a half of a block from Main Street, the beautiful Broadway fountain, and just three blocks from the river, Lanier Mansion, and Crystal Beach, Visitor’s Center and within walking distance of all of Madison’s event locations as well as historic properties.

The Porch at Milton

Escape to our charming 2-bedroom house, nestled along the serene banks of the river in Milton, KY. Whether you're looking to unwind or explore, this cozy home offers the perfect balance of comfort and nature's beauty. Best of all, you're just a 2-minute drive or a scenic 25-minute walk from the historic and charming downtown Madison, Indiana. Explore local shops, dine at unique restaurants, or stroll along the riverfront.