House holiday 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.

T&E Riverhouse Retreat

Experience the perfect blend of relaxation and recreation at our stunning property with panoramic river views. Enjoy direct beach access, where you can soak up the sun, swim, fish, kayak, and more. The home features upper/lower decks, a basketball goal, fire pit, and a kitchen on each level. Whether you're here for a peaceful getaway or an action-packed vacation, this riverfront retreat has everything you need for an unforgettable experience. Book your stay today and create lasting memories.

The Fashion House on Central

This beautiful historic home is in the heart of downtown Madison. It has been completely renovated with 4 large bedrooms and 3 full baths. This massive home is a show place and winner of the 2019 Historic Madison Inc. Preservation Award. The Fashion House is perfect for your family or friends gatherings with it's grand living and dining room. Madison features more historical blocks than any city in the US. We are also Indiana's Music City! You will be right in the heart of Main Street USA.

Main Street Retreat

Main Street Retreat offers a unique opportunity to immerse yourself in the beauty of Madison's historic district, all while enjoying the comforts of a home away from home. This homes Main Street prime location allows for easy access to live music, quaint shops, local eateries, walk along the river, and historic sites. Whether you're seeking a romantic escape, a girls trip, or a solo adventure, book your stay today and create lasting memories. One queen bed and couch are available for sleeping.

The Madison-Milton Cabin

Welcome to the Madison Milton Cabin. Enjoy a unique, peaceful setting just 5 minutes from Downtown Madison. Enjoy the great shopping, dining, and entertainment and finish your day relaxing next to a cozy outdoor fire. If you love sunsets you will love the views from the cabin. The house features a loft bedroom with comfy adjustable bed. The bathroom includes an oversized soaking Tub/Shower and the main living room includes a queen size pull out couch. Stay connected with high speed internet.

The Magnolia on Main hosted by Swell Stay

Featured on the Magnolia Network, this 1800’s property has been lovingly restored by the Beck Family. This 3 bedroom, 3.5 bath luxury residence has been thoughtfully designed with the Madison tourist in mind. Enjoy the view of the Main St parade from the 2nd and 3rd floors or spend time on the balcony watching the sun set on the majestic Ohio River. Centrally located on the Golden Block of Main Street in downtown Madison Indiana, you couldn’t stay in a more ideal location. Come stay awhile!

Glenda’s Overlook

Situated just one and a half blocks from the iconic Milton-Madison Bridge spanning the picturesque Ohio River, Glenda's Overlook offers the perfect retreat for you and your loved ones. Our home is located merely a few walking blocks, or short golf cart ride, from the historic district, and offers easy access to the city's charming wineries, shops, restaurants, Crystal Beach and vibrant festivals that Madison has to offer. Additionally, we are only a short drive to Clifty Falls State Park.

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 160 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.

Bicentennial Park View

New June 2024! Full time Airbnb. Come stay at this newly renovated home in historic downtown Madison. This 3-bed/2-bath home is adjacent to Bicentennial Park and includes a fully stocked kitchen, washer & dryer, internet, keyless entry, front porch that overlooks the Ohio River and more. From the front porch of this home, enjoy the festivities of live concerts and Friday-night movies. You will enjoy easy access to everything Main Street offers from this centrally located home.

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

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.