House vacation rentals in Jefferson County

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Top-rated house rentals in Jefferson County

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Top guest favorite

A spacious great room features a modern sectional sofa positioned around a circular coffee table atop a vibrant area rug. Large windows allow ample natural light, illuminating the vaulted ceiling with exposed beams. Complementary artworks and plants enhance the inviting ambiance.

Home in Madison

4.99 out of 5 average rating, 535 reviews

The Artist’s A-Frame

Get away and enjoy the comfort and convenience of this unique, newly remodeled A-Frame home nestled in a quiet, safe, upscale neighborhood, minutes from Clifty Falls State Park (10 min. drive), Historic Downtown (5 min. drive), hilltop shopping (5 min. drive): Hanover College (15 min. drive) •Fast Wi-Fi •Electric Fireplace .Two 55” Roku TVs, Complimentary YouTube TV for local and cable stations •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill

Top guest favorite

The exterior of the historic home features a brown brick façade with black shutters adorning the large windows. A red door is framed by a small porch with steps leading to the sidewalk. Potted red flowers add a pop of color to the entrance.

Home in Madison

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.

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, 23 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 the house features a covered front porch with two wooden chairs and a small table, surrounded by landscaped greenery. A light-colored brick facade is complemented by a black roof and accents. A pathway leads to the entrance, providing a welcoming approach.

Home in Madison

4.98 out of 5 average rating, 40 reviews

Annies river house!

Your group will enjoy Annies River House! Located on Main Street in beautiful historic Madison. We are just blocks from the majestic Ohio river, shopping, eateries and wineries! Rent a golf cart and maneuver through town with ease! Take in the history, the beauty and architecture of times past and know you have a comfortable spacious place to retire at the end of the day at Annies River House! Additional $10.00 per guest over two. One time fee. Additional $75.00 pet fee. One time fee.

Guest favorite

A golf cart is parked on a well-maintained lawn in front of a cozy home. A shaded seating area with a thatched roof is visible, along with an outdoor dining set. A cornhole game is set up on the grass beside the cart.

Home in Madison

4.94 out of 5 average rating, 71 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 view from the property showcases the Ohio River through large trees. A landscaped backyard features a dining area under a pergola with a gravel pathway. In the distance, recreational activities can be seen along the riverbank, adding to the vibrant outdoor atmosphere.

Home in Madison

4.98 out of 5 average rating, 151 reviews

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

Top guest favorite

The exterior of a charming shotgun house features a lavender-colored facade and a welcoming entrance. A small decorative plant is placed beside the steps, leading to a bright front door with a circular window above. Natural light enhances the inviting appearance.

Home in Madison

4.97 out of 5 average rating, 103 reviews

Lavender House

Newly renovated shot gun house, great location in downtown Madison Indiana. Only one block from Main Street where there is shopping and restaurants, and four blocks from the river front. Two bedrooms each with a queen size bed, one bath, fully stocked kitchen, small private backyard. Washer and dryer on site, on street parking.This property is a shotgun style home which means you walk through one bedroom to get to the next, but there is a door between.

Top guest favorite

Home in Madison

5 out of 5 average rating, 39 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!

Top guest favorite

The house exterior features a welcoming porch with two swings, framed by greenery from a nearby tree. Steps lead to the entrance, flanked by decorative lighting and elegant columns that provide a cozy, inviting setting.

Home in Madison

4.98 out of 5 average rating, 162 reviews

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.

Guest favorite

The exterior of the house is shown, featuring light grey siding and white trim. Two large windows are adorned with gray shutters, framed by a picket fence. A bicycle with a yellow frame leans against the fence, adding a pop of color to the scene.

Home in Madison

4.9 out of 5 average rating, 228 reviews

Rivertown Retreat in Historic Downtown

Located in beautiful, historic downtown Madison! Lisa and Richard co-own and co-host this adorable, recently updated Rivertown Retreat from the 1850s. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings Madison is famous for. Three blocks from the mighty Ohio. A short five-minute drive from Clifty Falls State Park. We fell in love with Madison and know you will, too.

Top guest favorite

A historic two-story home features a gray exterior with white columns supporting the porch. Lush green landscaping includes small bushes, with a paved pathway leading to the entrance. A wrought-iron fence encloses the yard, creating an inviting outdoor space.

Home in Madison

4.95 out of 5 average rating, 99 reviews

Watchmaker Place in Historic Madison District

This historic home is in the heart of downtown Madison. Watchmaker Place has been completely renovated while retaining its charm and elegance throughout. Located on beautiful West 2nd Street, less than two blocks from the river, restaurants, brewery, wineries, and downtown shopping. Convenient for festival activities or just a weekend away from it all.

Top guest favorite

A warm dining area features a wooden table surrounded by black chairs. Natural light brightens the space, reflecting off the polished wooden floor. A modern kitchen is visible in the background, equipped with stainless steel appliances and light cabinetry.

Home in Madison

5 out of 5 average rating, 185 reviews

Charming shotgun in the heart of downtown Madison

This charming, stylish 2-bedroom shotgun house is located on Main Street in historic downtown Madison, IN. You'll be just steps away from locally owned shops, bars, and restaurants, and within walking distance of the Ohio River and Madison's many festivals and events. Enjoy off-street parking, modern amenities, and the perfect front-porch view.