House vacation rentals in Jefferson County

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Top-rated house rentals in Jefferson County

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Guest favorite

An inviting exterior of The Olive House is displayed, featuring a covered porch with wooden beams. The landscaped grounds feature a winding stone pathway, bordered by fresh greenery and mulch, leading to the entrance. A serene atmosphere is created by the surrounding nature.

Home in Madison

5 out of 5 average rating, 17 reviews

The Olive House

Nestled in the heart of Madison's vibrant downtown district, The Olive House has timeless charm and modern comfort. Situated just steps away from a delightful array of eateries, antique boutiques, and the Ohio River, the Olive House comfortably accommodates up to 4 guests and the outdoor living area provides the perfect spot for relaxation. Experience the charm at The Olive House where every detail has been carefully curated to ensure a memorable stay that beckons you to return again and again.

Top guest favorite

The A-Frame home's exterior showcases a unique architectural design with a stone façade and a contrasting modern section. Large windows flank the entrance, allowing natural light to illuminate the interior. Lush greenery surrounds the property, enhancing its serene setting.

Home in Madison

4.99 out of 5 average rating, 518 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

Superhost

A cozy bedroom features a spacious bed topped with soft linens and decorative pillows. A wooden bench adds functionality at the foot of the bed. Wall decor includes various circular elements, while a colorful shade illuminates the room. A door leads to an adjoining space.

Home in Madison

4.88 out of 5 average rating, 8 reviews

Riverside Retreat - Steps to the River & Main St

Newly remodeled, well furnished, spacious home in the heart of everything going on in historic downtown Madison, Indiana. Steps from the river puts you on the doorstep of the Riverwalk and all the festivals on Vaughn Dr. Just 2 blocks to Main St makes an easy walk to all of the shopping, dining and festivals on Main St. Views of the Ohio River and Madison bridge are beautiful from the front and back of this home. Close to the public boat ramp and ample room for boat parking. Come stay with us!

Guest favorite

An inviting open space features an archway leading to a dining area with a wooden table surrounded by black chairs. Natural light filters through nearby windows, illuminating the room, which is adorned with animal-themed artwork. A staircase is visible in the background, accented by a potted plant.

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.

Guest favorite

A charming brick home is set against a grassy lawn, framed by a large tree. A tranquil pond is visible in the background, adding to the peaceful rural surroundings. The structure features a sloped roof and multiple windows, ensuring ample natural light.

Home in Hanover

4.93 out of 5 average rating, 15 reviews

The Hanover Haven - Slice of Paradise

Escape to this peaceful farmstead just outside of town for a truly relaxing getaway. The back porch is great for watching stunning sunsets over the pond and overlooking the active horse pasture! Stocked with top-quality fishery, it's a paradise for fishing enthusiasts. Nestled right up the road from Hanover College, 10 minutes from Historic Downtown Madison and Clifty State Park, and just 3 minutes from a local store. Book your stay now and enjoy the tranquility of this unique retreat!

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, 129 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

Guest favorite

The exterior of the house is shown, featuring light grey siding and white trim. Two large windows are adorned with gray shutters, framed by a picket fence. A bicycle with a yellow frame leans against the fence, adding a pop of color to the scene.

Home in Madison

4.9 out of 5 average rating, 212 reviews

Rivertown Retreat in Historic Downtown

Located in beautiful, historic downtown Madison! Lisa and Richard co-own and co-host this adorable, recently updated Rivertown Retreat from the 1850s. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings Madison is famous for. Three blocks from the mighty Ohio. A short five-minute drive from Clifty Falls State Park. We fell in love with Madison and know you will, too.

Guest favorite

The front exterior showcases a single-story historical house, featuring white brick and a charming entryway with a wooden door. Surrounding greenery includes well-maintained shrubs and a brick pathway leading to the entrance, complemented by light filtering through the leaves.

Home in Madison

4.85 out of 5 average rating, 20 reviews

Beautiful Bungalow on Main

Take it easy at this unique and tranquil getaway.A unique 150 yearls old Historical house on Main Street! SINGLE STORY !!This house is only few blocks away from downtown river walk. This property has a unique history and a very unique layout. It has almost a wrap-around front porch, and has ample character in its side and rear yards. Great lighting exists here, and the white shines throughout the indoors and outdoors.

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

4.86 out of 5 average rating, 143 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.

Guest favorite

The exterior of a historic home features a charming pink façade with white trim. Intricate woodwork adorns the porch, which is complemented by a wooden bench. A welcoming door with a decorative element is located at the center, framed by large windows.

Home in Madison

5 out of 5 average rating, 5 reviews

Little Pink House - North

This historic home from the 1890s has been completely remodeled, while still preserving its original hardwood floors and fireplace. The house features modern updates while retaining its original historic charm. It's located very close to the river, offering great views from both the front and back porches. Additionally, it's within walking distance of all the downtown amenities.

Top guest favorite

The front porch features black wrought-iron railings, a welcoming entry door with a decorative wreath, and a seating area with several chairs and a table. Lush greenery frames the entrance, enhancing the inviting look of the charming shotgun house.

Home in Madison

5 out of 5 average rating, 170 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.

Guest favorite

A decorative chandelier hangs from the ceiling, featuring an intricate black metal frame adorned with clear glass crystals. The lighting creates a soft glow, illuminating the surrounding room, which includes a dark dining table and white chairs in the background.

Home in Madison

5 out of 5 average rating, 18 reviews

The Whitehall Cottage

Relax with a peaceful river view during your stay! The home is fully furnished to accommodate your every need. Cottage is perfectly tucked away in a private corner of downtown. Yet close enough to quickly be part of majestic Madison. Golf cart is available for rental for an additional fee to complete your Madison getaway!