Pet-friendly vacation rentals in Madison

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, a bakery underneath the apt & 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!

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.

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

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!

Secluded Country Home in Historic Hoosier Hills

You’ll love the property because of the private secluded location and the views. The property is good for couples, solo families (with kids), all girls/boys gatherings and big groups. The house has over 1900 square feet of living space plus a sunroom looking over the pond and woods. There are two TVs with cable connection and one tv with an antenna. One TV is in the common living area and the other tv's are in two bedrooms, Catch and release fishing is permitted.

2 King Beds-1 Block to Main St-Downtown Cottage!

This renovated historic home features 2 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.

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.