Vacation rentals in Jefferson County

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Top-rated vacation rentals in Jefferson County

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Top guest favorite

A stone fireplace with a glass front is centrally located within a cozy living area, complemented by modern lighting fixtures. A small table with a decorative plant and items sits in front of the fireplace, enhancing the room's inviting ambiance.

Home in Madison

4.99 out of 5 average rating, 526 reviews

The Artist’s A-Frame

Get away and enjoy the comfort and convenience of this unique, newly remodeled A-Frame home nestled in a quiet, safe, upscale neighborhood, minutes from Clifty Falls State Park (10 min. drive), Historic Downtown (5 min. drive), hilltop shopping (5 min. drive): Hanover College (15 min. drive) •Fast Wi-Fi •Electric Fireplace .Two 55” Roku TVs, Complimentary YouTube TV for local and cable stations •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill

Top guest favorite

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

4.99 out of 5 average rating, 226 reviews

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.

Guest favorite

An arching stone bridge is visible, leading over a shallow creek. The area is surrounded by lush greenery and tall trees. Sunlight filters through the leaves, casting shadows on the rocky bank, adding to the natural setting. The bridge provides passage to hiking trails nearby.

Cottage in Madison

4.86 out of 5 average rating, 140 reviews

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Sue’s Cottage is a quaint two bedroom cottage with a porch over looking the Heritage Trail of Madison. It is perfect for pets. It is a home to many species of birds and wildlife. Relax on the deck bird watching or stroll through the heritage trail & scenic railroad tracks surrounding the cottage, which leads to the river walk. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. A portion of each stay is donated to local charity.

Top guest favorite

A landscaped backyard features a wooden pergola and various seating options. Lush greenery surrounds the area, offering a view of the Ohio River in the distance. A patio area is visible, creating a relaxed outdoor space for enjoyment.

Home in Madison

4.98 out of 5 average rating, 140 reviews

Riverview Historical Retreat

Full time Airbnb home in Historic Downtown Madison. This two bed, two bath home overlooks the Ohio River and includes a fully stocked kitchen, washer/dryer, screened in back porch, internet, keyless entry, and more Centrally located next to Bicentennial Park, enjoy one of the many restaurants, bars, parks, and local events, or enjoy a quiet weekend away with a weekly Music/Movie by the river, a local farmers market, and shops. There is something for everyone to enjoy in Madison

Top guest favorite

An open wooden gate reveals a serene outdoor space, featuring stone pathways and lush greenery. Potted shrubs flank the entrance, while patio furniture is positioned in the distance. A clear blue sky and soft clouds offer a bright backdrop to the inviting garden setting.

Guesthouse in Madison

4.99 out of 5 average rating, 268 reviews

Mulberry Cottage In The Heart Of Downtown Madison

This quaint studio cottage is located in the heart of Madison, Indiana. The entire building was fully renovated in 2020 and offers a modern luxurious stay in our beautiful historic town. This property features off-street parking, fast private WiFi, and complimentary beverages/snacks. Within walking distance of shopping, restaurants, and all downtown events. Few properties come close to the accessibility that this Madison cottage provides. We look forward to hearing from you!

Top guest favorite

A serene view of lush green trees stretches out, showcasing the natural landscape and rolling hills. The image captures the vibrant foliage under a partially cloudy sky, creating a peaceful atmosphere within the secluded setting.

Apartment in Madison

4.98 out of 5 average rating, 118 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.

Superhost

Two pendant lights hang from a wooden, vaulted ceiling, casting a warm glow over the kitchen area. A stainless steel refrigerator stands adjacent to a window dressed with a light blue curtain, above which is a charming display of autumn-themed artwork.

Cottage in Madison

4.9 out of 5 average rating, 179 reviews

Cozy Farmhouse Retreat in Historic District

Located in the Historic District in Madison! Lisa and Richard co-own and co-host this recently updated cottage. Welcome to our cozy, chic Farmhouse Retreat. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings for which Madison is famous. Only three blocks from the mighty Ohio and a short five-minute drive to Clifty Falls State Park. We fell in love with Madison and know you will, too.

Superhost

A well-lit bathroom is presented, featuring a wall-mounted mirror above a modern sink. A glass shower enclosure is located at the end of the room, with tile flooring extending throughout. Light beige walls create a clean and spacious feel.

Home in Madison

4.84 out of 5 average rating, 150 reviews

Carole's Cottage

Quaint cottage located in downtown Madison. A short walk to all shops & restaurants and beautiful riverfront. Guests have entire home including a screened in back porch to enjoy your morning coffee or just relax and read a book. Master bedroom has a king size bed and 2nd bedroom has a futon. Our kitchen is fully equipped, including stove, refrigerator, microwave and keurig coffee maker.

Top guest favorite

A covered porch features rustic wooden beams and a wide wooden deck. Two rocking chairs are positioned along the railing, accompanied by a potted plant displaying vibrant foliage. Light is captured through multiple windows set against the log cabin exterior.

Cabin in Madison

4.99 out of 5 average rating, 180 reviews

Stoney Creek Cabin - Sit back and unwind

Welcome to Stoney Creek Cabin. This charming 2 bedroom cabin is nestled in the hills of Madison, IN. Situated far enough away to offer all the privacy you want, yet only 8 miles from historic downtown, where there are so many gems nearby to explore. Enjoy the HOT TUB, wrap around porch, and patio! There could not be a more relaxing place to unwind.

Top guest favorite

A compact bathroom features a glass-enclosed shower, a small white vanity with a sink, and a toilet. Light-colored wood paneling adorns the ceiling, and white shiplap walls add brightness. A small rug is positioned in front of the vanity, with a modern light fixture above.

Home in Madison

5 out of 5 average rating, 178 reviews

Charming shotgun in the heart of downtown Madison

This charming, stylish 2-bedroom shotgun house is located on Main Street in historic downtown Madison, IN. You'll be just steps away from locally owned shops, bars, and restaurants, and within walking distance of the Ohio River and Madison's many festivals and events. Enjoy off-street parking, modern amenities, and the perfect front-porch view.

Top guest favorite

A circular wooden side table is positioned against a wall, featuring a coffee maker and a basket filled with assorted coffee pods. A decorative sign is placed beside the basket, adding a welcoming touch to the coffee station area.

Home in Hanover

4.93 out of 5 average rating, 185 reviews

Campus Cottage: Cozy, Convenient, Captivating

Charming ranch home on the edge of Hanover College campus. This 2 bed, 1 bath home contains hardwood flooring throughout, an eat-in dining area, open-concept living, and brand new furnishings. Explore the beauty of Hanover, just blocks from breathtaking Ohio River views, and 6 miles from Historic Downtown Madison.