Apartment holiday rentals in Jefferson County

A living area features a dark sofa adorned with scattered pillows, complemented by a wooden coffee table. Exposed brick walls bring a rustic charm, while large windows allow natural light to fill the space, showcasing views of the outside and nearby street.

4.98 out of 5 average rating, 58 reviews

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!

The exterior of a classic two-story building is featured, showcasing a combination of stone and white siding. Black window frames create a modern contrast, while the entrance is marked by a decorative sign reading 'The Madison Inn Circa 1925,' supported by stone walls and lanterns.

5 out of 5 average rating, 5 reviews

The Madison Inn, Est 1925 Historic suite 107

Discover the charm of Madison from our Est 1925 Historic Overlook Suite 107. Nestled in a prime location, this cozy 1-bedroom, 1-bathroom rental offers a perfect blend of comfort and convenience. Enjoy modern amenities such as a fully equipped kitchen, and laundry facilities to make your stay as comfortable as possible. Immerse yourself in the rich history and vibrant culture of Madison with this delightful retreat as your base. We are conveniently located close to all of the local attractions.

The living room features a brown leather sectional sofa arranged around a decorative coffee table with natural accents. Exposed wooden beams enhance the spaciousness, while a large mirror reflects light from nearby lamps. A brick wall adds character, complemented by wall art.

5 out of 5 average rating, 36 reviews

Livery Loft: BEST location!

This beautiful loft apt is spacious and guests say "it's beyond amazing"! 2+ bdrm 2 luxury bathrooms offer SO many amenities you won't want to leave! It has a very spacious living room, dining room & gourmet kitchen. The master bath has a fireplace above the soaking tub & a massage shower. The other bath has a rainfall shower and heated toilet seat: add luxury linens & you will feel very pampered! We have the best location just off main street and 3 blocks from the relaxing riverwalk.

A spacious living area features a large sectional sofa in a neutral gray shade. The wall is adorned with a decorative mirror and a rustic wooden accent, while warm lighting enhances the inviting atmosphere.

5 out of 5 average rating, 320 reviews

Stablemaster’s Quarters/ Best downtown location!

The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, a laundry room and a furnished white kitchen will all be appreciated. Carefully, the historic charm is blended within. You will soon see why the entire building is award winning! This fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the Midwest”.

The exterior view of the historic home showcases a charming two-story structure with a green facade and classic architectural details. A small pathway leads to the entrance, flanked by landscaped areas with shrubs. Nearby buildings exhibit a variety of colors, enhancing the neighborhood's character.

4.98 out of 5 average rating, 43 reviews

LarzHaus Suite

Located in historic downtown Madison, IN, the property is just one block from Main Street, and two blocks from the Ohio riverfront. You are 5 minutes to Clifty Falls State Park and 9 minutes from the Hospital and upper Madison area as well. THE AREA -This is an apartment located in the center of Downtown Madison Indiana, and is within walking distance of everything downtown has to offer. -This is a 2 apartment historical home, and is part of one of the largest historical districts in the USA.

The exterior of a historical building is visible, featuring a light-colored facade and multiple windows. The stone entryway displays an elegant sign naming 'The Madison Inn, Circa 1925.' Lantern-style light fixtures adorn the entrance, contributing to its classic charm.

5 out of 5 average rating, 12 reviews

The Madison Inn, Historic city overlook suite 206

Discover the charm of Madison from our Historic City Overlook Suite 206. Nestled in a prime location, this cozy 1-bedroom, 1-bathroom rental offers a perfect blend of comfort and convenience. Enjoy modern amenities such as a fully equipped kitchen, and laundry facilities to make your stay as comfortable as possible. Immerse yourself in the rich history and vibrant culture of Madison with this delightful retreat as your base. We are conveniently located close to all of the local attractions.

Superhost

A spacious studio suite is presented, featuring a queen-size bed with a white quilt, complemented by two chairs beside it. Large windows allow natural light, framed by gray curtains. A comfortable couch is positioned nearby, and a black television is mounted on the wall.

4.81 out of 5 average rating, 32 reviews

The Regatta Room (Unit 3) - Ohio River Views

Welcome to The Regatta Room by Parker Places! This luxury studio suite is recently remodeled and features brand new everything. It comes stocked with a full eat-in kitchen, new appliances, one queen-size bed, a comfy couch, TV, WiFi, and more. PRIME location with a view of the Ohio River, instant access to the walking path along the river, close to shops, cafes, & restaurants. PERFECT location for anything downtown, and it is just steps away from Madison's famous Regatta event.

Superhost

The exterior of The Madison Inn is presented, showcasing a three-story white building with large windows. A stone wall with black metal fencing frames the entrance, featuring a sign that reads 'The Madison Inn Circa 1925'. Lantern-style lights are mounted on the wall.

4.8 out of 5 average rating, 5 reviews

The Madison Inn, Historic woodside view suite 205

Discover the charm of Madison from the comfort of Historic Woodside view Suite 205. This cozy 1-bedroom, 1-bathroom rental is your perfect getaway, offering essential amenities to ensure a seamless stay. Enjoy the convenience of being close to all the local attractions. Unleash your culinary skills with our full kitchen or enjoy one of our local establishments. Nestled in a prime location, this suite promises a memorable stay for those seeking both relaxation and adventure.

The exterior of The Madison Inn is displayed, featuring a two-story white building with large black-framed windows. Stone walls provide a foundation, accompanied by black railings and lanterns that add character. The establishment is rooted in history, with the year '1925' elegantly inscribed.

4.91 out of 5 average rating, 35 reviews

Hometown on Main Street, Suite 102

Welcome to Hometown on Main, Suite 102, nestled in the heart of Madison. This cozy 1-bedroom, 1-bathroom rental is your perfect getaway, offering a blend of comfort and convenience. This room overlooks downtown Madison and is convenient to all the historic sites and local dining. Enjoy your morning coffee while overlooking downtown Main Street. Immerse yourself in the charm of Madison while enjoying the comforts of home. Ideal travelers or couples seeking a serene retreat.

An elegant building with a white exterior and black-framed windows stands behind a stone wall. The nameplate, 'The Madison Inn Circa 1925,' is prominently displayed in sleek lettering. Lantern-style lights are attached to the stone wall, adding charm to the entrance.

4.91 out of 5 average rating, 32 reviews

The Madison Inn, Sunset over the city Suite 201

Discover the charm of Madison from our cozy suite, "Sunset over the City" Suite 201. Perfect for couples or solo travelers, this 1-bedroom, 1-bathroom rental offers a beautiful view of Historic downtown Madison. Enjoy modern conveniences like a full kitchen for your culinary adventures, laundry facilities, and all the essentials. Located in the heart of Madison, you're perfectly positioned to explore the city's delights. Don't miss the breathtaking sunsets.

An indoor pool area is showcased with a bright sky and floor-to-ceiling windows offering scenic views of the surrounding hills. The pool is surrounded by tiled flooring and potted plants, creating a serene setting. Skylights enhance the natural light within the space.

4.99 out of 5 average rating, 162 reviews

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 exterior of The Madison Inn is highlighted, showcasing a contemporary structure with a streamlined design. The building features large windows and is framed by a decorative stone wall. Lanterns are positioned at the entrance, adding charm to the welcoming facade.