Apartment holiday rentals in Jefferson County

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Top-rated apartment rentals in Jefferson County

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Top guest favourite

Flat in Madison

4.98 out of 5 average rating, 247 reviews

Rivers Edge-Historic Hunger House-Upstairs-Madison

A unique blend of historic character and contemporary comfort! Floor to ceiling windows, amazing staircase and hardwood flooring with modern kitchen & bathroom, this UPSTAIRS unit with private entrance will be your oasis. The balcony, w/view of the Ohio river, is perfect for early morning coffee or relaxing after a busy day of touring Madison. WELCOME to the River's Edge! Extended stay (week-mo) discounts 21%-49%. Rent one or both floors (See "River's Edge II-listing) SEND INQUIRY FOR PRICING

Top guest favourite

Flat in Madison

5 out of 5 average rating, 29 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!

Top guest favourite

Flat in Madison

5 out of 5 average rating, 29 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.

Top guest favourite

Flat in Madison

5 out of 5 average rating, 309 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”.

Top guest favourite

Flat in Madison

5 out of 5 average rating, 34 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.

Superhost

Flat in Madison

4.84 out of 5 average rating, 19 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

Flat in Madison

5 out of 5 average rating, 3 reviews

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.

Guest favourite

Flat in Madison

4.89 out of 5 average rating, 28 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.

Guest favourite

Flat in Madison

4.89 out of 5 average rating, 19 reviews

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.

Top guest favourite

Flat in Madison

4.98 out of 5 average rating, 133 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.

Guest favourite

Flat in Madison

5 out of 5 average rating, 5 reviews

Southern view on Main suite 202

Discover the charm of Madison in our cozy Southern View on Main Suite 202. Nestled in a prime location, this 1-bedroom, 1-bathroom rental offers a perfect blend of comfort and convenience. Enjoy essential amenities like a fully equipped kitchen, and full laundry to make your stay as comfortable as possible. Whether you're in town for business or leisure, our suite is the ideal home away from home conveniently located to all the downtown attractions.

Superhost

Flat in Madison

4.86 out of 5 average rating, 14 reviews

Charolotte's Corner Overlook, Suite 101

Experience beautiful Mornings in this Corner suite. Rest with a beautiful view of Downtown or enjoy a peaceful stroll down Main Street. This suite is located right on Main Street a eating area, and is a great place for resting and relaxation. If you're looking for a local dining special. Then this room is conveniently located just a few blocks from entertainment and fine dining. This cozy suite is in the heart of Historic Madison.