Vacation rentals in Jefferson County

4.99 out of 5 average rating, 237 reviews

Two large riverboats are docked along the bank of the Ohio River, surrounded by greenery. A clear blue sky with white clouds sets the backdrop. The grassy area is shaded by broad trees, creating a serene view of the waterways and hills in the distance.

Apartment in Madison

Rivers Edge-Historic Hunger House-Upstairs-Madison

AshleyRating, 5 stars2 weeks ago

We loved our stay at Angela's place! As other's have said, she provides a lot of sweet, personalized touches that made our stay extra special. The apartment is very comfortable with a nice layout. The bedrooms are separated by the living area so if you like to watch TV late at night (like me) or are staying with another couple, you feel like you have your own space. Plus, the bedrooms are huge! The bathroom is also large with plenty of space to store your things. We had lots of rain so couldn't enjoy the porches but there are 3 outdoor spaces for hanging out. I wished I'd been able to enjoy the swing on the front porch! The parking right out back is great! Loved the location. You can walk everywhere easily. Despite rain, we walked to shopping, coffee shops, and restaurants. There is a trail that runs along the river that is a block or two away so if you are a runner, it's really nice. Clifty State Park is beautiful and just a few minutes away. I highly recommend Angela's place!

4.95 out of 5 average rating, 42 reviews

The Nature House

StephanieRating, 5 stars3 weeks ago

Jennifer’s place was a perfect stay for our family of seven. We had a kid with us and one of the rooms upstairs is connected to another room that has a futon. There isn’t a door that separates the two rooms but we were fine with that. It was sunny and nice to be able to sit on the back patio. We rented a golf cart and took that around town (designated areas). The town is very walkable and in the summer months, with everything open, I can imagine it being lively. We took a walk along the Ohio River (which we walked to) and that was nice. Kitchen also had what we needed to make meals. We would definitely stay here again.

4.99 out of 5 average rating, 218 reviews

The entrance features a red brick façade with a black front door and decorative glass panels. Two steps lead to the door, flanked by potted plants. The porch area is complemented by a wall-mounted light fixture and a welcoming atmosphere.

Townhouse in Madison

Cozy downtown home with patio. Walk to everything.

MartaRating, 5 stars3 weeks ago

Booked a last minute weekend get away with the family and we were not disappointed! The home was stunning, very clean, and had everything we could possibly need. We were so grateful for all of the baby supplies thoughtfully provided to reduce our packing: covered outlets, monitor, sound machine, pack n play with sheet, rocking chair, baby plates/bowls/utensils, and more. The kitchen was fully stocked and also had pantry staples as well! The only thing we could've asked for was a small card table & folding chair for our travel highchair and to contain the baby mess to the kitchen, but we made so no problem. :) Madison was a beautiful, little historic town and Ashley's home is right in the middle of downtown for easy walking. It's a small city so you don't have to worry about noise even though you're staying downtown. Overall we were so thankful for a cozy, easy stay in a beautiful historic home & town. Would stay again in a heartbeat!

4.98 out of 5 average rating, 103 reviews

Townhouse in Madison

209 King Beds, River View, Deck, Parking

ShellyRating, 5 stars5 days ago

Stayed for a girls weekend. We each had our own room and every place we wanted to go was within walking distance. We rented a golf cart but didn't really need it because of the location; however, the golf cart was super fun! Beautiful place. It's a tri-level with bedrooms in the lowest level, stairs to the main space, and stairs to the other two bedrooms. Absolutely gorgeous.

4.98 out of 5 average rating, 107 reviews

An outdoor deck features two chairs positioned beside a railing, overlooking a scenic view of the hills. Soft sunlight filters through the trees, illuminating the space and creating a peaceful ambiance for relaxation.

Apartment in Madison

The Treehouse - Hot Tub - Indoor Pool Get Away!

MelissaRating, 5 stars3 days ago

Pictures do not do this amazing home justice. It’s just magical. Sandy is soooo sweet and helpful. I can’t wait to go back! I felt like a Disney princess when the deer came strolling by. ❤️ peaceful beautiful surroundings and the pool is to die for! Thank you Sandy!

4.97 out of 5 average rating, 154 reviews

The Crafty Fox Den - Retreat House

DeniseRating, 5 stars3 weeks ago

A lovely, comfortable, spacious, artistically decorated and peaceful, this was a perfect spot for our team retreat. We loved the big family table for meetings and meals, the kitchen worked well for cooling together, 3 comfy sitting areas, 3 bathrooms and 3 bedrooms, plus walkable into sweet Madison and a short car ride to hike at Clifty Falls. we loved it!

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What guests are saying

The Regatta Room (Unit 3) - Ohio River Views

4.83 out of 5 average rating, 12 reviews2 months ago

It was exactly like the picture.She was very responsive for a question we had.Her book of attractions & where to eat made life easy.She puts a star by the one she would recommend.There was also a bulletin board on the wall with different menus.Very clean & updated.Would recommend & go back

Home in Madison

What guests are saying

3-suite cottage spa (aaaah!) house

5 out of 5 average rating, 48 reviews4 months ago

We loved our stay, Colene was the best host! She had so many great dinner recommendations and was responsive when I had questions! My family especially enjoyed the little snacks and treats she left for us. I would definitely recommend this place to anyone wanting to visit Madison! Her home was beautiful and provided the relaxing vacation our family was looking forward to! The house was spotless and there were so many amenities, the location was great and I loved that there is off the Main Street parking too! Great place and great host!

Cottage in Madison

What guests are saying

Livery Loft: BEST location!

5 out of 5 average rating, 24 reviews1 month ago

Beautiful Loft! We spent a few days here for our anniversary and the hosts were so thoughtful and decorated for our anniversary complete with a cake in the fridge for our arrival. It was clear that the hosts care very much about the comfort of their guests and they quite literally have thought of everything. We had fresh baked cookies and muffins the morning we left. We said that in all of the places we have stayed Ron and Suzie by far were the best hosts ever. We loved hearing the history of the building and strolling through town. Thank you so much for making this trip memorable!

Apartment in Madison

What guests are saying

Main Street Retreat Prime Location 3 Bedroom Top1%

4.97 out of 5 average rating, 29 reviews3 weeks ago

We loved our stay at Marcy‘s! It was the perfect walking distance from all the local shops on Main Street! Marcy’s kitchen was well equipped with all the things we needed to make breakfast, as well as coffee. The space was very clean, and looked like the pictures provided in the listing! Marcy provided multiple recommendations of things to do in the area and provided clear communication upon check-in and checkout. We would love to come and stay again next year!

Home in Madison

What guests are saying

The Whitehall Cottage

5 out of 5 average rating, 18 reviews4 months ago

We enjoyed our stay so much. The cottage is adorable and Carolina was so kind. We loved how close everything was and easy to get to. She had great recommendations for the local eateries and coffee shops. She was quick to respond if I had a question and check in/out was easy. We would love to visit Whitehall Cottage again.

Home in Madison

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Popular amenities for Jefferson County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Jefferson County

Superhost

A cozy living area is visible, featuring a light-colored sofa and a round wooden coffee table. A fan is mounted on the ceiling, and a light-colored rug covers the floor. Natural light enters through multiple windows, enhancing the warm wood tones of the walls.

Cabin in Madison

4.88 out of 5 average rating, 16 reviews

Peaceful Cozy Cabin

TylerRating, 5 stars6 months ago

it's the second time my girlfriend and I have stayed here and it's been great every time always will recommend a beautiful home and beautiful scenery

A winding country road is flanked by tall trees displaying vibrant autumn foliage in shades of yellow and orange. The damp pavement reflects the surrounding nature, while fallen leaves create a textured path beside the roadway. The scene conveys a sense of tranquility and connection to nature.

4.99 out of 5 average rating, 72 reviews

Cabin in the Holler

Hyun JiRating, 5 stars1 week ago

Pauline’s place was so beautiful! It had everything listed and Pauline herself was so sweet! We didn’t have to worry about privacy as the property had so much space and the check in and out process was extremely easy. It is also located close to Madison, IN which had great restaurants and a great downtown (You will need a car to get to downtown). Overall would love to stay again.

5 out of 5 average rating, 66 reviews

Guest suite in Hanover

OFF THE CLOCK River House

KylieRating, 5 stars6 months ago

Amazing hosts! Great place with a beautiful view! Incredibly friendly and helpful and we had the best time! Thank you!!

The front entrance of the house features a black door with a lantern on either side. A small pumpkin is placed on the step, and greenery borders the entrance. Two additional structures are visible in the background, complementing the historic aesthetic.

5 out of 5 average rating, 18 reviews

Annies Fabulous Federal house

KateRating, 5 stars5 days ago

The federal house was the perfect landing spot for a weekend away. The house was comfortable and well stocked. It was a great locatiom to be able to walk to dinner and the river.

4.93 out of 5 average rating, 61 reviews

A view from the loft features a log railing overlooking a rustic dining area. Natural wood tones and beams accentuate the space, while a wooden table set for dining is visible below, accompanied by a bouquet of flowers and a hanging light fixture above.

Cabin in Madison

Historic 1830s Log Cabin in Madison, IN

JenniferRating, 5 stars5 days ago

This getaway was just as cute in person as is in the pictures. The rich history of the location and original architecture of the cabin left us speculating about the first owners. Really neat to see. Don and Michelle were quick with communication and responses. Didn't have any issues with our stay or this property. (PLEASE read reviews that mention the stairs to the beds/lofts. 😉)

A contemporary two-story home features a dark exterior with large windows and a striking red front door. Well-maintained landscaping surrounds the property, with neatly arranged stone pathways leading to the entrance. A serene sunset casts a warm glow on the structure.

5 out of 5 average rating, 13 reviews

2 Master Suites w/sleeper sofa! Spacious Getaway!

JarrodRating, 5 stars1 week ago

This house was amazing and everything is updated. It’s within walking distance from everything which is great. Highly recommend this place!

The exterior of a single-story cottage is displayed, featuring light yellow siding and blue shutters. A solid black trash bin is positioned next to the door, which is framed by a small porch area and has a nearby gravel path leading to the entrance.

4.95 out of 5 average rating, 41 reviews

The little house

AlyssaRating, 5 stars1 week ago

Korey's place was exactly as described! Cozy place and big enough for my husband and I and our two dogs. Great location, extremely walkable to all of the fun spots downtown. Would definitely stay here again, such a great price!

Superhost

A bathroom features a curved wooden vanity topped with granite. A round mirror is mounted above, framed in dark wood. Towels hang on decorative rings beside the sink, and a shelf holds neatly arranged toiletries. Natural light brightens the soothing blue walls.