Vacation rentals in Jefferson County

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.

4.99 out of 5 average rating, 527 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

A historic staircase with wooden banisters leads to the upper level, featuring white risers and dark brown treads. A sign indicating 'PRIVATE NO ENTRY' is displayed prominently on the stairway. The background reveals a glimpse of a yellow-painted room with a sink and black wall hanging.

5 out of 5 average rating, 146 reviews

River's Edge II-Historic Hunger House-Downstairs

Newly renovated DOWNSTAIRS unit of this historic home in the heart of downtown Madison. Experience the unique blend of historic character and contemporary comfort! Relax on our front porch (complete with swing and river view) after a busy day of touring shops, historic sites, cultural, or music festivals that are the heart of Madison... WELCOME to the River's Edge II! Extended stay (wk-mo) discounts 21%-49% Rent one or both floors (See "River's Edge-UPSTAIRS-listing) SEND INQUIRY FOR PRICING.

4.99 out of 5 average rating, 226 reviews

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

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.

4.86 out of 5 average rating, 141 reviews

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

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.

4.95 out of 5 average rating, 21 reviews

A covered back porch features a round table with matching chairs and two cushioned lounge chairs with floral patterns. The porch overlooks a serene pond and well-maintained lawn, creating a peaceful outdoor space for relaxation.

Home in Hanover

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!

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.

4.98 out of 5 average rating, 141 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

4.99 out of 5 average rating, 269 reviews

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

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!

The image captures a serene view of a bridge framed by bare trees, characteristic of winter. The background features rolling hills, and the Ohio River can be glimpsed through the branches, adding to the tranquil setting.

4.98 out of 5 average rating, 119 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, 180 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.

4.99 out of 5 average rating, 180 reviews

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

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.

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.

5 out of 5 average rating, 180 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.

4.93 out of 5 average rating, 187 reviews

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

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.

Vacation rentals for every style

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Popular amenities for Jefferson County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Jefferson County

Superhost

An outdoor dining area features a rustic wooden bar adorned with vintage signage and colorful decorative lights. Reclaimed wood tables are positioned in front, inviting gatherings. Surrounding foliage creates a natural backdrop, while an old blue refrigerator adds character to the space.

4.5 out of 5 average rating, 10 reviews

Lucky Shamrock

Mairice and MakaiRating, 5 stars1 month ago

My son and I enjoyed staying at the lucky shamrock! I loved the porcelain bathtub. Terry was so sweet and nice. Our first night we realized the fridge didn’t get cold enough . We contacted Terry and she was very prompt in responding back and getting a new fridge and her handyman Mike was very nice and gave info on great eating places we enjoyed. I loved that there was a washer and dryer since we stayed for about a week here. Ideal location to fun things to do in Madison. We loved it!! It was very peaceful! That couch was so comfy and great napping. The quilt was beautiful!

An open-concept living area is depicted, featuring a modern kitchen with dark cabinetry and stainless steel appliances. Two pendant lights hang above a kitchen island with seating for four. A glass coffee table and a plush gray sofa complete the inviting ambiance.

4.97 out of 5 average rating, 61 reviews

Glenda’s Overlook

AdrianRating, 5 stars6 days ago

Everything was lovely! Thank you!

A spacious studio suite is presented, featuring a comfortable queen-size bed and a cozy couch situated across from a kitchenette with modern appliances. Natural light floods the room through a large window, while a bathroom doorway is visible in the background, enhancing the open layout.

4.87 out of 5 average rating, 15 reviews

The Regatta Room (Unit 3) - Ohio River Views

JerriRating, 5 stars3 weeks ago

The area was amazing with shops, restaurants & museums. Short drive to downtown. The walks along the Ohio River were amazing! Would stay here again if coming to Madison! 😊

4.95 out of 5 average rating, 59 reviews

Bicentennial Park View

DouglasRating, 5 stars3 days ago

great place to stay. parked my car off street under a carport and never moved it. The river walk along the mighty Ohio was one block away and good shopping, restaurants and historic architecture best seen on foot was right there. house was clean and they thought of all the little details to make a comfortable stay. Well equipped kitchen. would definitely stay again. Also friendly neighbors and area

4.83 out of 5 average rating, 12 reviews

A large two-story home is set against a bright blue sky, showcasing a brick facade and a spacious driveway. The front yard features green grass and well-maintained landscaping. Large windows allow natural light to fill the interiors.

Home in Hanover

The Hanover O-Asis

PatsiRating, 5 stars2 months ago

This home looked new, very clean and open. The extras, games, snacks, coffee were great. we could walk to Hanover College which was why we were there. Road noise mentioned in the listing was so minimal, we really never noticed. This home is beautiful and very comfortable. Will absolutely go back when we visit grandaughter in college!

4.98 out of 5 average rating, 50 reviews

A spacious bathroom features a glowing air jet tub filled with bubbles, surrounded by soft lighting and candles. A comfortable chair and a small table are positioned nearby, inviting relaxation. The bedroom area is visible in the background, showcasing a serene ambiance.

Cottage in Madison

3-suite cottage spa (aaaah!) house

LeslieRating, 5 stars5 months ago

We loved our stay, Colene was the best host! She had so many great dinner recommendations and was responsive when I had questions! My family especially enjoyed the little snacks and treats she left for us. I would definitely recommend this place to anyone wanting to visit Madison! Her home was beautiful and provided the relaxing vacation our family was looking forward to! The house was spotless and there were so many amenities, the location was great and I loved that there is off the Main Street parking too! Great place and great host!

A decorative centerpiece is displayed on a table, featuring a glass candle surrounded by black, spiky accents. Pine cones are arranged alongside natural greenery, adding texture and warmth to the setting.

5 out of 5 average rating, 27 reviews

Livery Loft: BEST location!

TerryRating, 5 stars1 week ago

Our stay at Ron and Suzie's Livery Loft was exceptional. Certainly one of the top rentals we have ever had. The theme and decor was perfect for a Livery Loft concept, with top quality furnishings and just an overall outstanding atmosphere. We have never had a rental with so many amenities, fine touches, and hospitable personal service. On top of that, the location was walkable to downtown shopping and restaurants. Madison has really come along as a destination! We just really can't say enough positives, and there are literally no constructive improvement comments that we could think of. Certainly an awesome experience and can't wait to stay in Ron and Suzie's place again!