House vacation rentals in Jefferson County

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.

4.99 out of 5 average rating, 528 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

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.

4.99 out of 5 average rating, 92 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.

The exterior of the home features a charming blue facade and a welcoming front door with a decorative glass accent. A brick pathway leads to the entrance, bordered by neatly trimmed greenery and potted plants. Lush shrubbery frames the property, enhancing its inviting appeal.

5 out of 5 average rating, 73 reviews

The Book Haven - A Book Lover's getaway near Main

Spacious & stylish period home furnished like you’re traveling back in time - or escaping it. With an eclectic mix of decor from antique federalist style to fun MCM, the owners designed it to feel like a cozy library. Ready to see historic Madison? Walk 3 mins to Main St where you’ll find the Attic, Mad Love, Trolley Barn, & Olde Tyme. On Saturday mornings, take a 7-min stroll through Madison’s most stately brick homes down Third through Mill, Vine, Elm, and Broadway to the Farmer’s Market.

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.

4.97 out of 5 average rating, 64 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 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.

4.95 out of 5 average rating, 65 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.

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.

4.98 out of 5 average rating, 143 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

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.

4.97 out of 5 average rating, 158 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.

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.

4.9 out of 5 average rating, 220 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.

The exterior of a cozy cottage is showcased, featuring a light green brick facade. A short set of stairs leads up to the front door, complemented by a black railing. The surrounding area includes black mulch and shrubs, with blue skies visible above.

4.97 out of 5 average rating, 29 reviews

Coming Home Cottage

Welcome to Coming Home Cottage, your charming retreat in the heart of historic downtown Madison, Indiana. This cozy cottage offers the perfect home away from home, located only one block from Main Street and easy access to all of downtown Madisons many shops and festivals, while being just minutes away from the modern Madison hilltop. Come and enjoy a short stroll to all Madison has to offer.

The exterior of the cottage features a light gray facade with decorative trim. Two sets of black shutters adorn the windows, and a small porch with a railing is visible at the entrance. The street is bordered by trees and neighboring houses.

4.84 out of 5 average rating, 151 reviews

Carole's Cottage

Quaint cottage located in downtown Madison. A short walk to all shops & restaurants and beautiful riverfront. Guests have entire home including a screened in back porch to enjoy your morning coffee or just relax and read a book. Master bedroom has a king size bed and 2nd bedroom has a futon. Our kitchen is fully equipped, including stove, refrigerator, microwave and keurig coffee maker.

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.

4.95 out of 5 average rating, 97 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.

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.