Holiday rentals with a patio in Trimble County

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 Nature House

Historic home located in downtown Madison. Walking distance to all the shops, dining, and riverfront. The house is clean and beautifully decorated. Perfect for couples or groups. Modern kitchen with all the amenities you will need. Beautiful deck and patio out back with comfortable furniture and a fully fenced yard. The decor was inspired by Mother Nature and each room is decorated with gorgeous animal prints. Three bedrooms with comfortable mattresses and an office with a convertible couch.

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!

The Baltmore

Experience the charm of an 1800's shotgun style home in Madison's National Historic District. This home was completely remodeled yet maintains its historic character. All of the artwork and decor was purchased locally and pays homage to Madison and its vibrant arts community. Located in a quiet neighborhood yet just a few walkable blocks away from the heart of downtown Madison's shops, restaurants and lively music scene. Perfect for a small family, couples or girlfriend getaway.

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.

"Madison Manor II” Hot Tub, Patio, Fire Pit, Grill

This spacious Italianate style townhouse is nestled in the heart of downtown Madison just 2 blocks from the river and steps from restaurants, shops, and more. Rent a golf cart and live like a local! NEW: Game room with mini theater! The home is beautifully furnished with ample amenities for optimal guest comfort & convenience. The decor reflects the city’s rich steamboat history. Adjoins Madison Manor I which can be booked separately. Shared patio with hot tub, fire pit, grill.

The Regatta Room (Unit 3) - Ohio River Views

Welcome to The Regatta Room by Parker Places! This luxury studio suite is recently remodeled and features brand new everything. It comes stocked with a full eat-in kitchen, new appliances, one queen-size bed, a comfy couch, TV, WiFi, and more. PRIME location with a view of the Ohio River, instant access to the walking path along the river, close to shops, cafes, & restaurants. PERFECT location for anything downtown, and it is just steps away from Madison's famous Regatta event.

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

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.