Holiday rentals with a patio in Jefferson County

Laid Back Getaway at Summer's Place

Currently decorated for Christmas and ready for you to experience the holidays here in historical Madison. The cottage is located just steps away from the beautiful Heritage Trail and one block from Main Street; nestled at the end of a quiet street with minimal traffic -four blocks to the river. Madison offers many festivals & community events. You'll be close enough to walk and far enough to enjoy your peace & quiet. Restaurants, stores and great coffee shops are all in walking distance.

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.

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.

Studio apartment above Garage in downtown Madison

This special place is located in downtown Madison. It's steps from restaurants and walking distance across all of downtown Madison. This above the garage apartment overlooks a koi pond and beautiful backyard of one of Madison's historic homes. Enjoy the beautiful balcony views and relax in this studio efficiency apartment with a pull out couch. Walking distance to gorgeous hiking destinations, including Clifty Falls State Park and the Heritage Trail. Come enjoy all that Madison has to offer!

The Magnolia on Main hosted by Swell Stay

Featured on the Magnolia Network, this 1800’s property has been lovingly restored by the Beck Family. This 3 bedroom, 3.5 bath luxury residence has been thoughtfully designed with the Madison tourist in mind. Enjoy the view of the Main St parade from the 2nd and 3rd floors or spend time on the balcony watching the sun set on the majestic Ohio River. Centrally located on the Golden Block of Main Street in downtown Madison Indiana, you couldn’t stay in a more ideal location. Come stay awhile!

The Book Haven - A Book Lover's getaway near Main

Spacious & stylish period home furnished like you’re traveling back in time - or escaping it. With an eclectic mix of decor from antique federalist style to fun MCM, the owners designed it to feel like a cozy library. Ready to see historic Madison? Walk 3 mins to Main St where you’ll find the Attic, Mad Love, Trolley Barn, & Olde Tyme. On Saturday mornings, take a 7-min stroll through Madison’s most stately brick homes down Third through Mill, Vine, Elm, and Broadway to the Farmer’s Market.

Glenda’s Overlook

Situated just one and a half blocks from the iconic Milton-Madison Bridge spanning the picturesque Ohio River, Glenda's Overlook offers the perfect retreat for you and your loved ones. Our home is located merely a few walking blocks, or short golf cart ride, from the historic district, and offers easy access to the city's charming wineries, shops, restaurants, Crystal Beach and vibrant festivals that Madison has to offer. Additionally, we are only a short drive to Clifty Falls State Park.

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.

Romantic Retreat w/ Hot Tub-5 min from downtown

Soak in your private hot tub under the stars while the firepit glows beside you — the perfect romantic escape just 5 minutes from Madison’s historic riverfront. This cozy cottage combines luxury touches (Sleep Number bed, massage chair, spa-style extras) with unforgettable experiences: stargazer projector, outdoor movie nights, and complimentary first bundle of firewood. Upgrade your stay with our romance, outdoor movie or fall picnic experience! Pls note: must be 25 to rent.

The Goataway

Quaint and delightful guesthouse in downtown Madison within walking distance of all the activities and amenities our convivial town has to offer. Perfect for a couple but room for 3 on two large living room sofas. Bessi and Aberforth (aka Abe), the owners goats, live in the backyard seen from the eat-in kitchen. They are super friendly and always up for attention. The space is refreshing, bright and comfortably furnished. You’ll have everything you need for a pleasant stay.

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 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.