Holiday rentals with outdoor seating in Madison

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.

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.

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Sue’s Cottage is a quaint two bedroom cottage with a porch over looking the Heritage Trail of Madison. It is perfect for pets. It is a home to many species of birds and wildlife. Relax on the deck bird watching or stroll through the heritage trail & scenic railroad tracks surrounding the cottage, which leads to the river walk. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. A portion of each stay is donated to local charity.

Madison's only Yurt experience!!!

You'll love this unique and romantic escape in the hills of southern Indiana! Located just 20 minutes from beautiful downtown Madison and Vevay. Enjoy the countryside in your very own yurt. Come relax after a hard day of shopping in downtown Madison or after a late night at Belterra casino. You will love the warm inviting boho style of decor while enjoy the beautiful sunsets from the deck. The stars look so close you could touch them from the grassy hillsides of this enchanting property.

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 Goataway

Quaint and delightful guesthouse in downtown Madison within walking distance of all the activities and amenities our convivial town has to offer. Perfect for a couple but room for 3 on two large living room sofas. Bessi and Aberforth (aka Abe), the owners goats, live in the backyard seen from the eat-in kitchen. They are super friendly and always up for attention. The space is refreshing, bright and comfortably furnished. You’ll have everything you need for a pleasant stay.

Cozy Farmhouse Retreat in Historic District

Located in the Historic District in Madison! Lisa and Richard co-own and co-host this recently updated cottage. Welcome to our cozy, chic Farmhouse Retreat. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings for which Madison is famous. Only three blocks from the mighty Ohio and a short five-minute drive to Clifty Falls State Park. We fell in love with Madison and know you will, too.

Hilltop Dome, 42 secluded acres in nature

Our Geodome is tucked away on 42 private acres exclusively for you and your guest Enjoy the stars at night, fire pit, hot tub, high speed internet, washer dryer, heat and air-conditioning and all the amenities. We are conveniently located within 15 miles of Madison, IN, Vevay, IN, Clifty Falls, Belterra Casino, also within 62 miles of Cincinnati and Louisville.

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.