House holiday rentals in Jefferson County

This Airbnb is next-level. The kitchen is absolutely gorgeous—fully stocked, spacious and perfect for cooking big meals. The bedrooms are huge, with super comfy beds that made it hard to leave in the morning. We loved sitting in the hot tub, hanging out around the fire pit, and spending a quiet morning on the grand front porch. The saltwater pool wasn’t open yet, but it looked amazing—we’ll definitely be back when it's ready to use. The man cave was the perfect hangout spot—It’s got a pool table, foosball, poker table, big comfy couch, large TV, and even a fridge for snacks and drinks. We spent many hours in there! The basement is a fun zone with arcade games, karaoke, darts and so much more. Almost impossible to be bored while staying here. A huge shoutout to Deb, the best host we could’ve asked for—super kind, thoughtful, and incredibly accommodating. We loved every minute of our stay and are already looking forward to coming back!

The “Derby Winner” was a wonderful and fitting home for our stay. 4 bedrooms—all with king size beds—was perfect for our group of four adults. The outdoor space and amenities were exactly what we were looking for, as well. It was a very comfortable and relaxing space. Tony & Danielle are amazing hosts and we’re always responsive to our needs and requests. Would absolutely recommend this home for anyone looking for a nice stay!

This is a great place to stay, peaceful and quiet! Pool, hot tub, and bar came in handy when relaxing The margarita maker was clutch lol Dustin is always responsive when needed!

The house absolutely beautiful. So incredibly clean. Lots of space for our family.

Lisa and Bobby were excellent hosts. They helped me feel at home, provided great recommendations and offered to personally show me around my new state. The check in was simple, rooms clean, and amenities well stocked. I appreciate the time and care they took to make the transition easier for me. Thank you!

Cyndi’s a great host. The photos accurately portray the space, no surprises. Fit well for my family of 5 and 3 pets. Too bad it wasn’t summer, the pool is right off the primary bedroom. Would definitely recommend!

Patrick was an extremely responsive post. This house by far exceeded our expectations! It is so beautifully decorated and is the most well stocked home we have ever stayed in! We were all very comfortable and enjoyed everything about this home!

This place was amazing. Both Wes and Rachel were extremely accommodating and had everything we needed ready. The place was clean and stocked with everything to make our stay perfect. The boat ride down the river made for a memorable highlight. We will be back!

We had a great girls weekend! Madison is a super cute, friendly, eclectic community. This home was super adorable, super comfy, and a great place to have a comfy, fun, relaxing girls weekend.

Could'nt have asked for a better place for a girls getaway to Madison! Charming, cozy yet extremely spacious and immaculate historic home, so roomy, close to everything from walking to Main St. to driving just minutes to the Lanier Mansion. John is friendly, responds quickly and very helpful. Absolutely recommend the Jefferson Retreat!

Very nice place, well-kept especially for being a historic place. Cool history of being a “shotgun house.” Convenient downtown location. Plenty of living space, including the living room and multiple bedrooms.

We stayed at Renae’s place for a short getaway from Louisville with our son. We wanted to “ chill” someplace and spend time together, and Renae’s place proved to be the perfect place for this! The Cottage is beautifully done and very well- outfitted. Really lovely. We had game night and movie night - all provided there. And the waffle bar and eggs in the morning were a wonderful treat. Renae was extremely responsive and helpful. Highly recommend for a relaxing get away with all the comforts!

Angela’s place was great! Walking distance to downtown Madison, she was more than willing to provide great recommendations for us. The deck was wonderful to sit on during a nice evening as well! We will definitely be back.

We had a wonderful girls weekend! Great location. Easy walk to Main St. Spacious and clean with the most comfy beds. Would definitely stay here again!!

Immediate responses from Brooke when we had questions. Fabulous location with walking distance to downtown. Very spacious accommodations with nice outside sitting area and fenced yard.

This rental has everything you need and quality products to make the stay enjoyable. All those little touches made it so nice--the nespresso machine, quilted toilet paper, le creuset pans, phone charger cords, nice mattresses, local spices for cooking, and local art on the walls to enjoy! We felt right at home and would not hesitate to return. Easy walking distance to fountain, Main St shops and restaurants, parks, etc. Easy parking on street. Private patio in backyard to enjoy when weather cooperates.

Nestled along the serene banks of the Ohio River, Fiona’s Boho Retreat offers a perfect blend of tranquility and comfort, creating an ideal escape for those looking to unwind, recharge, and disconnect. With its bohemian-inspired decor and cozy, nature-filled surroundings, this charming hideaway allows you to relax while surrounded by the beauty of the river and the sounds of nature.

Great location and easy walk to town and the Ohio river. Grandson wanted to walk to "Ohio" alot. Close to Clifty Falls. We would stay here again if back in the area.

We had a great stay. Beds were comfy and all amenities were as described.

The little pink house was an incredible place to stay. The cleanest Airbnb I’ve ever stayed at. Location was incredible to downtown and the river. Ashton and Addison went above and beyond when I asked for their help on a birthday surprise upon arrival. Great host and great spot. If I come back to Madison this is where I’ll be staying.

Beautiful home. Great location. Early check in was unexpected and I really appreciated that. Communication spot on. I hope to stay here again. I would definitely recommend Annie’s River House. 10 Stars!!!!❤️

My husband and I really enjoyed our stay at The Baltmore. The house was immaculate, and the decor was so tastefully done. From the local artists artwork throughout the house, the comfortable and cozy furniture, most from local vendors and shops in Madison, and the special decorating touches that made you feel right at home. The booklet that she put together had not only great suggestions for restaurants and things to see and do in Madison but also had the history of the house. The neighborhood was very quiet and close to absolutely everything in Madison. We loved sitting out on the back deck just enjoying the pleasant evenings. Andra was an incredible host, by far one of the best I have ever dealt with on Airbnb. She was so helpful and always responded to my emails very quickly. She definitely does what it takes for you to be comfortable and feel like you're in your own home. I highly recommend it if you're planning a trip to Madison, IN.

I had a fantastic stay at Sankalp’s Airbnb in Madison, Indiana. The entire space has been beautifully renovated, blending modern touches with cozy charm. The dining area was stunning, and the full kitchen was fully equipped and functional—perfect for preparing meals. The living room was inviting and thoughtfully laid out, with stylish furniture that made it easy to relax and unwind. The bathroom was impressively spacious, featuring a gorgeous sink and a beautifully designed shower that felt spa-like. I also appreciated the washer and dryer combo, which made doing laundry quick and convenient. The bedroom was equally impressive, with a large, comfortable bed, a lovely desk, and a well-designed layout that made the room feel both open and peaceful. Every detail of the home was carefully considered and beautifully executed. Overall, this Airbnb was exceptional, and I will absolutely be staying here again the next time I visit Madison!

Very easy to communicate with our host and everything was very clean and comfortable!