Pet-friendly vacation rentals in Jefferson County

"Madison Manor II” HotTub +Walk to Downtown, River

Madison Manor II is a spacious historic townhouse just 2 blocks from the Ohio River, 5 blocks to the boat ramp, & a short walk to charming downtown Madison. One of the only homes in town with both a hot tub & game room, it sleeps up to 8 -- perfect for families & small groups. Enjoy vintage character, modern comforts, a shared patio with hot tub, fire pit & grill, plus a mini-movie theater, dartboard, & more. Madison Manor II adjoins Madison Manor I—book both homes together for larger groups.

Walnut Street Saloon BNB

Step back in time to enjoy a historic tavern-turned-getaway in downtown Madison, Indiana. This spacious home, once a bustling town staple, combines rich history with modern amenities. Immerse yourself in Madison's vibrant heritage while staying just blocks away from locally owned shops, bars, and restaurants, as well as the beautiful Ohio River. It's the perfect vacation spot, whether you're here to shop, explore Clifty Falls State Park, or check out one of Madison's many festivals and events.

The little house

Located right in downtown historic Madison just a few blocks from the river, great restaurants, bars, hiking trails and all the different events going on In Madison. Full kitchen, washer dryer, and a firepit with seating out back, everything you could need for a relaxing stay! *House was previously smoked in as a rental and a guest at the beginning of my Airbnb journey. I am working diligently on removing the smell. I just disclaimer for anyone that is super sensitive to light cigarette smoke*

The Nature House

Historic home located in downtown Madison. Walking distance to all the shops, dining, and riverfront. The house is clean and beautifully decorated. Perfect for couples or groups. Modern kitchen with all the amenities you will need. Beautiful deck and patio out back with comfortable furniture and a fully fenced yard. The decor was inspired by Mother Nature and each room is decorated with gorgeous animal prints. Three bedrooms with comfortable mattresses and an office with a convertible couch.

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.

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.

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

Mulberry Cottage In The Heart Of Downtown Madison

This quaint studio cottage is located in the heart of Madison, Indiana. The entire building was fully renovated in 2020 and offers a modern luxurious stay in our beautiful historic town. This property features off-street parking, fast private WiFi, and complimentary beverages/snacks. Within walking distance of shopping, restaurants, and all downtown events. Few properties come close to the accessibility that this Madison cottage provides. We look forward to hearing from you!

The Main St. Oasis - Heart of Downtown Madison

Welcome to the Main St. Oasis in the heart of Historic Downtown Madison! We're steps away from Lanthier Winery, shopping, fine dining, the Ohio River, & have a coffee shop right across the street. Close to Clifty Falls State Park (3 min) & Hanover College (9 min). Enjoy a unique retro-western theme, with games & luxuries for all ages. Perfect for couples, families, or small groups. Ideal for exploring Madison’s top attractions or relaxing in comfort right on Main St!

The Cottage by the Woods

This small but newly renovated Cottage by the Woods offers a peaceful country alternative to an airbnb stay. The cottage is lightly decorated for seasonal transitions. It is located 15 minutes from downtown Madison, IN. A partial wrap around deck allows for a tranquil cup of coffee while bird watching. Free WiFi and Roku TV is provided along with other small amenities including various flavored coffee's for your morning cup of joe and a waffle making station.

The Porch at Milton

Escape to our charming 2-bedroom house, nestled along the serene banks of the river in Milton, KY. Whether you're looking to unwind or explore, this cozy home offers the perfect balance of comfort and nature's beauty. Best of all, you're just a 2-minute drive or a scenic 25-minute walk from the historic and charming downtown Madison, Indiana. Explore local shops, dine at unique restaurants, or stroll along the riverfront.

Fiona’s Boho Retreat

Did you ever wish your decor showed your quirky side? That’s what we’ve done. If Pottery Barn decor is your vibe you will be disappointed BUT if your adventurous side likes eclectic,boho meets MCM space that’s not perfect but perfectly imperfect, this is for you. 3.5 blocks to the tourist area and 4 blocks from the river. Quiet street and pet friendly.