Vacation rentals with a patio in Jefferson County

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Top-rated patio rentals in Jefferson County

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Top guest favorite

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

4.96 out of 5 average rating, 24 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.

Top guest favorite

An historic black-and-white photograph depicts a two-story brick building with a sign reading 'Walnut St. Saloon.' In front, a horse-drawn wagon is positioned beside a man sitting on it, while another man stands by the building entrance.

Home in Madison

5 out of 5 average rating, 96 reviews

Walnut Street Saloon BNB

Step back in time to enjoy a historic tavern-turned-getaway in downtown Madison, Indiana. This spacious home, once a bustling town staple, combines rich history with modern amenities. Immerse yourself in Madison's vibrant heritage while staying just blocks away from locally owned shops, bars, and restaurants, as well as the beautiful Ohio River. It's the perfect vacation spot, whether you're here to shop, explore Clifty Falls State Park, or check out one of Madison's many festivals and events.

Top guest favorite

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.

Home in Madison

4.99 out of 5 average rating, 105 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.

Top guest favorite

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.

Home in Madison

5 out of 5 average rating, 30 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!

Top guest favorite

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.

Home in Madison

4.96 out of 5 average rating, 75 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.

Guest favorite

An outdoor seating area features a round table surrounded by four metal chairs. A tall, grass-like sculpture stands nearby, complemented by a wooden railing and a concrete patio. The view of the hills in the background adds to the setting.

Home in Madison

4.92 out of 5 average rating, 75 reviews

Your Madison Home Away from Home

While staying in this cozy home, you can enjoy a peaceful morning with a small view of the Ohio River then use the golf cart to explore the historic town. Take a leisurely stroll along the Ohio River waterfront, visit the local winery, or indulge in the local restaurants and cafes nearby. Whether you're visiting Madison for a weekend getaway or a business trip, our home offers the perfect blend of comfort, convenience, and local charm. Book your stay today and make unforgettable memories.

Top guest favorite

A fenced back patio is shown, featuring a patio table with four chairs beneath a shaded umbrella. Paved with bricks, the space includes potted plants and a heating lamp, creating a welcoming area for relaxation outdoors.

Townhouse in Madison

4.99 out of 5 average rating, 239 reviews

Cozy downtown home with patio. Walk to everything.

Your family will be close to everything in downtown Madison when you stay at this conveniently located, updated home built in 1880. First floor open concept floor plan includes living room equipped w/electric fireplace and an eat-in kitchen w/bar stool seating for 4. Upstairs offers two bedrooms and full bath w/shower and old old-fashioned soaker tub. Enjoy nice weather on the fenced back patio. Note: This property contains stairs and is not recommended for guests with mobility issues.

Top guest favorite

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.

Home in Madison

4.95 out of 5 average rating, 38 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.

Guest favorite

A log cabin with a charming wood exterior is framed by lush greenery. The front porch features wooden railings and a welcoming entrance. A seasonal decoration is positioned beside the pathway, adding a touch of character to the inviting entrance.

Cabin in Madison

4.98 out of 5 average rating, 54 reviews

Cedar Rustic Cabin at Lost Trails

This cabin is nestled with 4 other cabins, tucked into 45 acres of wooded forest. It is minutes to Madison's Historic Downtown district. Walking trails, ponds and daily wildlife sightings make this stay a peaceful & serene getaway from the hurriedness of daily living. Offering a full kitchen, washer and dryer & family room with double recliner, this one-bedroom cabin is perfect for two people. The wraparound deck provides comfortable seating to relax & enjoy beautiful views!

Top guest favorite

Guesthouse in Madison

4.93 out of 5 average rating, 100 reviews

The Goataway

Quaint and delightful guesthouse in downtown Madison within walking distance of all the activities and amenities our convivial town has to offer. Perfect for a couple but room for 3 on two large living room sofas. Bessi and Aberforth (aka Abe), the owners goats, live in the backyard seen from the eat-in kitchen. They are super friendly and always up for attention. The space is refreshing, bright and comfortably furnished. You’ll have everything you need for a pleasant stay.

Top guest favorite

An indoor pool area is showcased with a bright sky and floor-to-ceiling windows offering scenic views of the surrounding hills. The pool is surrounded by tiled flooring and potted plants, creating a serene setting. Skylights enhance the natural light within the space.

Apartment in Madison

4.99 out of 5 average rating, 142 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Top guest favorite

Home in Madison

5 out of 5 average rating, 46 reviews

Romantic Retreat w/ Hot Tub-5 min from downtown

Soak in your private hot tub under the stars while the firepit glows beside you — the perfect romantic escape just 5 minutes from Madison’s historic riverfront. This cozy cottage combines luxury touches (Sleep Number bed, massage chair, spa-style extras) with unforgettable experiences: stargazer projector, outdoor movie nights, and complimentary first bundle of firewood. Upgrade your stay with our romance, outdoor movie or fall picnic experience!