Vacation rentals with a fireplace in Madison

Luxury Historic Home Ping Pong, Decks, Walkable

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.

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.

The Cabin

As you walk in, The Cabin wraps it's arms around you and says " Welcome home." You can feel the stress leave you as you settle in for your stay at this scenic cabin on 9.8 wooded acres. Fully furnished, spacious 1 room cabin with stone wood burning fireplace, equipped kitchen, bath with shower and twin over queen bunk bed. Refresh your mind & soul on the covered back porch overlooking the mature woods. Enjoy watching the abundant wildlife, including turkeys, deer, chipmunks and squirrels.

Cabin on the Ridge

Welcome to Cabin on the Ridge, your tranquil retreat nestled in the scenic hills of Madison, Indiana. Just 25 minutes from downtown Madison, our cabin offers a perfect blend of rustic charm and modern comfort. Madison, awarded the “Best Small Town in the Midwest” by USA Today and the Great American Main Street Award, is a must-visit. Enjoy the historic architecture, boutique shops, and delightful eats, or explore Clifty Falls State Park. •Fast wifi •Roku TV/Streaming services •Keurig

Cedar Rustic Cabin at Lost Trails

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

Secluded Country Home in Historic Hoosier Hills

You’ll love the property because of the private secluded location and the views. The property is good for couples, solo families (with kids), all girls/boys gatherings and big groups. The house has over 1900 square feet of living space plus a sunroom looking over the pond and woods. There are two TVs with cable connection and one tv with an antenna. One TV is in the common living area and the other tv's are in two bedrooms, Catch and release fishing is permitted.

Vineyard Château - peaceful country setting!

Forget your worries in this spacious and serene space. A beautiful three bedroom home, located between two historic towns of Vevay and Madison, Indiana. Perfect location for some rest & relaxation. Private country setting, just a short drive away from antiques, restaurants, state parks, and Splinter Ridge Hunting Reserve. Please note: The home is located 13 miles east of downtown Madison, approximately a 20 minute drive.

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.

Annies Fabulous Federal house

Annies Fabulous 1850 Federal house is just blocks from the majestic Ohio River, shopping, eateries and wineries! Step out the front door and be a part of the largest historic district in Indiana! Annies Fabulous Federal house has fabulous upgrades, fabulous decor, and a semi -private back patio! We allow canines! $75.00 upcharge for your dog will be added.