Vacation rentals with a patio in Trimble County

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Top-rated patio rentals in Trimble County

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A shaded patio area is visible, furnished with several cushioned chairs and a table. The view of the river stretches beyond vibrant flower beds. A staircase can be seen leading to the upper level, under the patio's roof.

Home in Hanover

4.88 out of 5 average rating, 8 reviews

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.

Superhost

A cozy bedroom features a spacious bed topped with soft linens and decorative pillows. A wooden bench adds functionality at the foot of the bed. Wall decor includes various circular elements, while a colorful shade illuminates the room. A door leads to an adjoining space.

Home in Madison

4.88 out of 5 average rating, 8 reviews

Riverside Retreat - Steps to the River & Main St

Newly remodeled, well furnished, spacious home in the heart of everything going on in historic downtown Madison, Indiana. Steps from the river puts you on the doorstep of the Riverwalk and all the festivals on Vaughn Dr. Just 2 blocks to Main St makes an easy walk to all of the shopping, dining and festivals on Main St. Views of the Ohio River and Madison bridge are beautiful from the front and back of this home. Close to the public boat ramp and ample room for boat parking. Come stay with us!

Guest favorite

Home in Madison

4.95 out of 5 average rating, 42 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.

Top guest favorite

Home in Madison

5 out of 5 average rating, 5 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!

Guest favorite

An outdoor deck is softly illuminated by string lights, featuring a vibrant mix of yellow, red, and black adirondack chairs arranged around a central table. A colorful area rug lies beneath the seating, creating a cozy atmosphere for gatherings.

Home in Madison

4.96 out of 5 average rating, 51 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.

Top guest favorite

A historic home is displayed with a charming façade featuring red accents, including a front door and window frames. Black shutters adorn the windows, and a decorative light fixture is positioned next to the door. The image captures a replica of the home held in front for contrast.

Home in Madison

4.97 out of 5 average rating, 29 reviews

Main Street Retreat Prime Location 3 Bedroom Top1%

Enjoy a relaxing experience at this centrally-located historic home. The Retreat offers an opportunity to immerse yourself in the beauty of Madison's historic district, all while enjoying the comforts of a home away from home. The 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 girl's trip, weekend getaway book your stay today and create lasting memories.

Top guest favorite

A cozy outdoor seating area features a dark wicker sectional sofa with gray cushions surrounding a glass-topped table. A yellow watering can and potted plants add touches of color, while a vibrant red umbrella provides shade. The blue exterior of the nearby house completes the inviting space.

Home in Madison

5 out of 5 average rating, 27 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.

Top guest favorite

Home in Madison

4.94 out of 5 average rating, 51 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.

Top guest favorite

The exterior of a charming Italianate-style townhouse is displayed, featuring a symmetrical facade with large windows adorned with black shutters. A vibrant red door adds a pop of color. Lush greenery surrounds the entrance, complementing the rustic brick exterior under a clear blue sky.

Townhouse in Madison

4.92 out of 5 average rating, 26 reviews

"Madison Manor I” By the River *Regatta Special

*Regatta Special* ~Noon check-in to start the party early ~2 chilled local beer growlers ~Late check-out. This spacious Italianate townhouse is nestled in the heart of downtown Madison just 2 blocks from the river. The house is beautifully furnished with ample amenities for optimal guest comfort & convenience. The decor reflects the rich train history of the city. The home adjoins Madison Manor II which can be booked separately. Shared patio includes hot tub, fire pit, gas grill.

Superhost

The exterior of the triplex features two levels with a light grey facade and contrasting red doors. A staircase leads to a balcony with seating, while gravel surrounds the building. Lush greenery and a hillside are visible in the background.

Home in Madison

4.83 out of 5 average rating, 12 reviews

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.

Guest favorite

A view of the Ohio River is captured from a front porch, showcasing a serene landscape with trees lining the riverbank. A pathway runs alongside the river, leading to a white archway structure. The distant bridge is visible, contributing to the tranquil setting.

Cottage in Madison

4.97 out of 5 average rating, 36 reviews

Cheerful 3-Bedroom cottage with fireplace.

UPDATED: Riverfront Retreat | Walk to Downtown | Festivals, History & Nature Escape to this newly renovated riverfront gem, where modern comfort meets historic charm! Enjoy breathtaking water views and an unbeatable location just steps from Main Street. Stroll to boutique shops, local dining, and live music, or explore nearby parks, trails, and historic sites. Whether you seek relaxation or adventure, this home offers the perfect base to experience the best of Madison!