Pet-friendly vacation rentals in Jefferson County

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 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.

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.

Fiona’s Boho Retreat

Did you ever wish you could decorate for your own personal pleasure? Our kids are grown so that’s what we’ve done! If you are searching for Pottery Barn decor you will be disappointed BUT if your adventurous side likes eclectic,boho meets MCM space that’s not perfect but perfectly lived in, this is for you. Walkable to downtown, 3.5 blocks to the beginning of the tourist area and 4 blocks from the river. On a quiet street,great neighbors and pet friendly. We hope you enjoy!

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.

Historic 1830s Log Cabin in Madison, IN

Beautiful historic 1830s log cabin nestled in the woods of Dugan Hollow! A 2-story cabin with 2 authentic lofted bedrooms, an indoor jacuzzi tub, fireplace and baby grand piano. Uniquely situated only 5 minutes from Historic Madison, Indiana on the Ohio River; 15 minutes from Clifty Falls State Park; and 20 minutes from Big Oaks National Wildlife Refuge. *Small dogs allowed with prior approval, see below.*