House holiday rentals in Jefferson County

Laid Back Getaway at Summer's Place

Our historical cottage, built in 1900, has been recently remodeled and located just steps away from the beautiful Heritage Trail. You will be nestled at the end of a very quiet street with minimal through traffic. Just four blocks to the Ohio River and one block from Main Street. Madison is known for its many festivals /community events. You'll be close enough to walk and far enough to enjoy your peace & quiet. Many restaurants, stores & three great coffee shops are all in walking distance.

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

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 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 Rosa Stay a Historic Gem in Downtown Madison

Enjoy a stylish experience at the Rosa Stay. This remodeled gem blends timeless Italian architecture with modern charm. Whether you’re visiting Madison for a weekend escape, a romantic retreat, or a solo recharge, this 1-bedroom, 1-bathroom home offers a stay that’s one of a kind. The home has a thoughtful open floor plan. The kitchen and living room share one cozy space, perfect for late-night wine or morning coffee. Upstairs, you’ll find the bedroom and bathroom in a loft-style layout.

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

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! Pls note: must be 25 to rent.

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.

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.

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.

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.

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.