Holiday rentals with a patio in Jefferson County

Main Street Retreat

Main Street Retreat offers a unique opportunity to immerse yourself in the beauty of Madison's historic district, all while enjoying the comforts of a home away from home. This homes Main Street prime location allows for easy access to live music, quaint shops, local eateries, walk along the river, and historic sites. Whether you're seeking a romantic escape, a girls trip, or a solo adventure, book your stay today and create lasting memories. One queen bed and couch are available for sleeping.

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.

Your Madison Home Away from Home

While staying in this cozy home, you can enjoy a peaceful morning with a small view of the Ohio River then use the golf cart to explore the historic town. Take a leisurely stroll along the Ohio River waterfront, visit the local winery, or indulge in the local restaurants and cafes nearby. Whether you're visiting Madison for a weekend getaway or a business trip, our home offers the perfect blend of comfort, convenience, and local charm. Book your stay today and make unforgettable memories.

3-suite cottage spa (aaaah!) house

Treat yourself to a feel-good gathering place for up to six. Our well-stocked kitchen will support your meals together, with concierge food services upon request, cappuccinos by Breville Barista Touch and more nice extras. Linen sheets, feather pillows and comforts abound. Rest well and take time for a soak in the air jet tub or an oversized stone tub. (Be sure to try the Toto Washlet, too!) — Madison has so much to offer, but you may simply want to bask in pampered retreat at Stay Lello.

The Hanover Haven - Slice of Paradise

Escape to this peaceful farmstead just outside of town for a truly relaxing getaway. The back porch is great for watching stunning sunsets over the pond and overlooking the active horse pasture! Stocked with top-quality fishery, it's a paradise for fishing enthusiasts. Nestled right up the road from Hanover College, 10 minutes from Historic Downtown Madison and Clifty State Park, and just 3 minutes from a local store. Book your stay now and enjoy the tranquility of this unique retreat!

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.

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

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!

Watchmaker Place in Historic Madison District

This historic home is in the heart of downtown Madison. Watchmaker Place has been completely renovated while retaining its charm and elegance throughout. Located on beautiful West 2nd Street, less than two blocks from the river, restaurants, brewery, wineries, and downtown shopping. Convenient for festival activities or just a weekend away from it all.