Pet-friendly holiday 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.

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.

Bicentennial Park View

New June 2024! Full time Airbnb. Come stay at this newly renovated home in historic downtown Madison. This 3-bed/2-bath home is adjacent to Bicentennial Park and includes a fully stocked kitchen, washer & dryer, internet, keyless entry, front porch that overlooks the Ohio River and more. From the front porch of this home, enjoy the festivities of live concerts and Friday-night movies. You will enjoy easy access to everything Main Street offers from this centrally located home.

Main Street - Heart of downtown Madison!

Main St is the HEART of Madison! We are centrally-located in downtown Madison. Our home is within walking distance for all of your downtown shopping adventures and the beautiful Riverfront. Start your mornings with a walk to one of our local coffee shops on your way to shop or enjoy a peaceful morning in of our amazing parks. Lunch and dinner can be their own adventure with all the local downtown eateries. Located only a few minutes away from the beautiful Clifty Falls State Park!

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

OFF THE CLOCK River House

OFF THE CLOCK RIVER HOUSE is a rare find among Air BnB options. Our riverfront property is ideal for ALL water activities; boating, jet skiing, kayaking, fishing, and swimming. A private concrete launching ramp and a large dock with a double jet ski dock are located directly in front of our home. Of course, you can also enjoy the gentle flow of this peaceful, riverside escape allowing yourself to unwind and recharge. Historic Madison offers many options to explore.

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 Hanover Hideaway

Discover the perfect retreat in Hanover, less than a mile from Hanover College, minutes from Clifty Falls State Park, 6 miles to the Ohio River Boat Ramp & less than 10 minutes to Historic Downtown Madison. This 3-bed, 2-bath home embodies modern Western design, offering comfort and style. Ideal for extended trips or weekend getaways. Whether you're here for academia or leisure, we promise you will enjoy your stay at the Hanover Hideaway!

~2 KingBeds+1 Block to MainSt+Privacy Fence~

🏠 This updated historic home features two bedrooms, both with king beds, and one full bathroom with a washer and dryer. The home is clean and charming, sure to be just what you need for a family trip, girls' weekend, or romantic getaway! 🚸 Enjoy a brief walk to all that downtown Madison, Indiana has to offer. It is also a quick drive to Madison's hilltop, Hanover College, and Clifty Falls State Park. 🚙 On street parking only.