Pet-friendly holiday rentals in Jefferson County

4.94 out of 5 average rating, 63 reviews

Cabin in Madison

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 with irregular shaped stairs as per the photos. Boasts a luxurious, oversized indoor jacuzzi tub for two. 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. *Price based on double occupancy. Small dogs allowed with prior approval, see below.*

5 out of 5 average rating, 82 reviews

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.

4.92 out of 5 average rating, 51 reviews

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*

4.97 out of 5 average rating, 34 reviews

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 $20.00 per guest over two. One time fee. Additional $50.00 pet fee. One time fee.

4.86 out of 5 average rating, 141 reviews

Cottage in Madison

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.

4.95 out of 5 average rating, 59 reviews

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.

4.99 out of 5 average rating, 69 reviews

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!

4.98 out of 5 average rating, 141 reviews

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

Superhost

Home in Deputy

4.84 out of 5 average rating, 25 reviews

Hardy Lake Vacation House

The House sits On Hardy Lake. 2 beds, 2 bath. Inside it has a full kitchen . The living room has queen sized sofa beds for extra guests. Gas grill and wood burning Fire pit, hot tub. Self-check-in. Smart TV that gets local channels. We provide board games, playing cards. Quiet getaway where guests can simply relax away from the city. 15 minutes from Scottsburg IN, 50 minutes from Louisville Ky. Lakeside Camping 4 min, Hardy Lake public Beach 15 min.boat parking space available

4.99 out of 5 average rating, 269 reviews

Guest house 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!

5 out of 5 average rating, 66 reviews

Guest suite in Hanover

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.