Holiday rentals with outdoor seating in Trimble County

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 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!

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

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.

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.

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.

Little Pink House - South

This historic home from the 1890s has been completely remodeled while still preserving its original hardwood floors and fireplace. The house features modern updates while retaining its original historic charm. It's located very close to the Ohio River, offering great views from both the front and back porches. Additionally, it's within walking distance of all the downtown amenities.

Little Lamb Retreat at the river

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!!!

209 King Beds, River View, Deck, Parking

Stay at General’s Quarters (209) — a stylish 3-level home in historic downtown Madison! Just steps from the Ohio River, Bicentennial Park, shops, bars, and restaurants. Sleeps 10 with 4 bedrooms & 3.5 baths. Enjoy modern comforts, fast Wi-Fi, a full kitchen, reserved parking and walkable access to festivals and local charm. Perfect for families or group getaways!