Vacation rentals with a patio in Trimble County

A charming entrance of the home is shown, featuring a maroon-colored exterior and a covered porch. An American flag gently flutters above, while a walkway leads toward the Ohio River visible in the background, framed by trees and a peaceful landscape.

4.98 out of 5 average rating, 43 reviews

River Living - Beautiful Views of the River

Peaceful Retreat or Heart of the Activity There is easy access to all things Madison from this beautifully updated, well furnished, centrally located home Only 2 blocks to Main St shops, dining & festivals Just feet from the Ohio River puts you on the doorstep of the Riverwalk & all festivals on Vaughn Dr Unobstructed, breathtaking views of the Ohio River & Madison Bridge Just 200 ft to public boat ramp & street parking spacious enough for a boat makes this a boaters dream This home has it all!

4.95 out of 5 average rating, 20 reviews

A multi-level house is situated on a hillside, offering a wide deck with railings and large windows. Surrounding greenery and shrubs are visible, complementing the natural landscape. A clear blue sky serves as the backdrop, enhancing the peaceful ambiance of the property.

Home in Hanover

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.

A cozy bedroom features exposed brick walls and wooden flooring. A spacious bed is adorned with a light blanket and a decorative pillow. A television is positioned on a dresser opposite the bed, and a seating area is visible in the corner.

4.99 out of 5 average rating, 99 reviews

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.

A spacious living area features light blue walls and a comfortable sectional sofa. Natural light flows through the large windows, illuminating the room. An area rug with floral patterns lays on the hardwood floor, complemented by artwork depicting animals on the walls.

4.95 out of 5 average rating, 44 reviews

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 exterior of the property features historic architecture with large, elegant windows. Decorative elements are visible along the façade, and potted plants are placed outside the entrance. The vibrant colors of the building contrast with the greenery of the surrounding trees.

5 out of 5 average rating, 24 reviews

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 exterior of a modern two-story house features a dark blue brick facade, accented by large arched windows. A wooden entrance is framed by a covered porch, leading to a well-maintained landscaped area with tidy gravel, small shrubs, and ornamental plants.

4.96 out of 5 average rating, 70 reviews

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.

A charming shotgun style home features a light blue exterior with white trimming and a covered front porch. The porch is adorned with plants and a small seating area. A pathway leads to the entrance, framed by a neat garden and wrought iron railing.

4.94 out of 5 average rating, 34 reviews

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.

A covered porch features a six-seat wrought iron dining set, providing a shaded space for outdoor gatherings. The flagpole displays the American flag against a clear blue sky. Surrounding greenery adds a touch of nature, enhancing the welcoming exterior of the home.

4.93 out of 5 average rating, 69 reviews

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.

4.86 out of 5 average rating, 21 reviews

A spacious studio suite is presented, featuring a queen-size bed with a white quilt, complemented by two chairs beside it. Large windows allow natural light, framed by gray curtains. A comfortable couch is positioned nearby, and a black television is mounted on the wall.

Apartment in Madison

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.

4.82 out of 5 average rating, 34 reviews

A charming brick townhouse is displayed, with contrasting black shutters and red doors. Decorative elements, including patriotic wreaths and bunting, adorn the windows. Lush greenery and a mulched garden area add to the inviting exterior, complemented by a clear blue sky above.

Townhouse in Madison

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

This spacious Italianate townhouse is nestled in the heart of historic downtown Madison just 2 blocks from the river and steps from charming restaurants, shops, wineries, and more. Rent a golf cart and live like a local! The house is beautifully furnished with ample amenities for optimal guest comfort & convenience. The decor reflects the city’s rich train history. Home adjoins Madison Manor II which can be booked separately. Shared patio with hot tub, fire pit, and grill.