Vacation rentals in Jefferson County

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Top-rated vacation rentals in Jefferson County

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Top guest favorite

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

4.99 out of 5 average rating, 240 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

Guest favorite

An aerial view of a historic home showcases its two-story structure, featuring a light-colored exterior with contrasting dark window frames. The surrounding snow-covered ground and nearby greenery provide a serene backdrop, while the road is visible in the distance.

Home in Madison

4.95 out of 5 average rating, 42 reviews

The Nature House

Historic home located in downtown Madison. Walking distance to all the shops, dining, and riverfront. The house is clean and beautifully decorated. Perfect for couples or groups. Modern kitchen with all the amenities you will need. Beautiful deck and patio out back with comfortable furniture and a fully fenced yard. The decor was inspired by Mother Nature and each room is decorated with gorgeous animal prints. Three bedrooms with comfortable mattresses and an office with a convertible couch.

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, 224 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.

Top guest favorite

Cabin in Madison

4.98 out of 5 average rating, 717 reviews

Cabin on the Ridge

Welcome to Cabin on the Ridge, your tranquil retreat nestled in the scenic hills of Madison, Indiana. Just 25 minutes from downtown Madison, our cabin offers a perfect blend of rustic charm and modern comfort. Madison, awarded the “Best Small Town in the Midwest” by USA Today and the Great American Main Street Award, is a must-visit. Enjoy the historic architecture, boutique shops, and delightful eats, or explore Clifty Falls State Park. •Fast wifi •Roku TV/Streaming services •Keurig

Top guest favorite

A view from the property showcases the Ohio River through large trees. A landscaped backyard features a dining area under a pergola with a gravel pathway. In the distance, recreational activities can be seen along the riverbank, adding to the vibrant outdoor atmosphere.

Home in Madison

4.98 out of 5 average rating, 133 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

4.98 out of 5 average rating, 265 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

The spacious living area is furnished with a large sectional sofa and an ottoman, complemented by decorative pillows. A mix of historic photographs adorns the walls, while natural light enters through a large window. A desk with a lamp and a Bluetooth speaker add functionality.

Townhouse in Madison

4.98 out of 5 average rating, 104 reviews

209 King Beds, River View, Deck, Parking

General’s Quarters (209) is situated steps from the Ohio River. This renovated 3-level historic (circa 1830) home is a perfect (and spacious) gathering place for families and friends. We're located near all the festival action (Bicentennial Park) and easy walking distance to Main Street and bars and restaurants. Clifty State Park is a quick drive to the west side of town. GQ includes 4 bedrooms (2-King Suites, 2-Queen) and Queen sleeper sofa in the living room.

Top guest favorite

A modern structure features large glass windows with views of the surrounding greenery. The deck is lined with a railing and includes outdoor seating. Tall trees stand nearby, contributing to the secluded atmosphere of the property.

Apartment in Madison

4.98 out of 5 average rating, 112 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

The kitchen area showcases modern stainless appliances and dark cabinetry. A large kitchen island with stools for four is highlighted, alongside reclaimed wood accents. Bright blue walls create a lively atmosphere, and sliding barn doors provide a unique touch to the space.

Cottage in Madison

4.9 out of 5 average rating, 177 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.

Top guest favorite

Home in Madison

4.97 out of 5 average rating, 156 reviews

The Crafty Fox Den - Retreat House

Nestled in Madison, Indiana’s beautiful historic district. The home is a newly renovated four square craftsman, located in the middle of town, still quiet and cozy. You are a half of a block from Main Street, the beautiful Broadway fountain, and just three blocks from the river, Lanier Mansion, and Crystal Beach, Visitor’s Center and within walking distance of all of Madison’s event locations as well as historic properties.

Guest favorite

The exterior of the cottage features a light gray facade with decorative trim. Two sets of black shutters adorn the windows, and a small porch with a railing is visible at the entrance. The street is bordered by trees and neighboring houses.

Home in Madison

4.85 out of 5 average rating, 146 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 wide wrap-around porch features several wooden rocking chairs, perfect for relaxation. The porch is adorned with rustic wooden beams and overlooks a grassy area with potted plants, surrounded by trees displaying autumn foliage.

Cabin in Madison

4.99 out of 5 average rating, 178 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.