Holiday rentals with a fireplace in Jefferson County

The Olive House

Nestled in the heart of Madison's vibrant downtown district, The Olive House has timeless charm and modern comfort. Situated just steps away from a delightful array of eateries, antique boutiques, and the Ohio River, the Olive House comfortably accommodates up to 4 guests and the outdoor living area provides the perfect spot for relaxation. Experience the charm at The Olive House where every detail has been carefully curated to ensure a memorable stay that beckons you to return again and again.

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

River Living - Beautiful Views of the River

Peaceful Retreat or Heart of the Activity There is easy access to all things Madison from this beautifully updated, well furnished, centrally located home Only 2 blocks to Main St shops, dining & festivals Just feet from the Ohio River puts you on the doorstep of the Riverwalk & all festivals on Vaughn Dr Unobstructed, breathtaking views of the Ohio River & Madison Bridge Just 200 ft to public boat ramp & street parking spacious enough for a boat makes this a boaters dream This home has it all!

The Madison-Milton Cabin

Welcome to the Madison Milton Cabin. Enjoy a unique, peaceful setting just 5 minutes from Downtown Madison. Enjoy the great shopping, dining, and entertainment and finish your day relaxing next to a cozy outdoor fire. If you love sunsets you will love the views from the cabin. The house features a loft bedroom with comfy adjustable bed. The bathroom includes an oversized soaking Tub/Shower and the main living room includes a queen size pull out couch. Stay connected with high speed internet.

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.

2 King Suites Luxury Historic Home, decks, games

Nestled in the heart of historic Madison, Indiana, this nineteenth-century home has stood proudly at the corner of Fifth and Mulberry Streets for more than 150 years. Where others saw a crumbling house, we saw potential. Through a true labor of love, this historic gem was thoughtfully restored, honoring its original character while breathing new life into every corner. The home blends timeless architecture with modern comfort, an inviting space full of history, warmth, and renewed beauty.

Modern Nature Cabin | Private Escape in the Forest

Escape to this charming 1BR/1BA retreat at Pole Barn, where rustic character blends with cozy, modern amenities. Nestled in a peaceful setting, it’s ideal for a relaxing getaway, creative retreat, or quiet work-from-home escape. The space features a comfortable bedroom, spotless bathroom, convenient kitchenette, and tranquil views of nature. Just minutes from Hanover College and historic downtown Madison, IN — perfect for exploring local shops, dining, and scenic riverfront walks!

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!

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.