Vacation rentals with outdoor seating in Jefferson County

The historic home features a classic brick exterior with intricate architectural details and large windows. A welcoming front porch is supported by white columns, enhancing the entrance. Surrounding greenery adds to the inviting atmosphere of this thoughtfully renovated property.

4.99 out of 5 average rating, 147 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.

A cozy bedroom features exposed brick walls and wooden flooring. A spacious bed is adorned with a light blanket and a decorative pillow. A television is positioned on a dresser opposite the bed, and a seating area is visible in the corner.

4.99 out of 5 average rating, 91 reviews

Main Street Retreat

Main Street Retreat offers a unique opportunity to immerse yourself in the beauty of Madison's historic district, all while enjoying the comforts of a home away from home. This homes Main Street prime location allows for easy access to live music, quaint shops, local eateries, walk along the river, and historic sites. Whether you're seeking a romantic escape, a girls trip, or a solo adventure, book your stay today and create lasting memories. One queen bed and couch are available for sleeping.

An outdoor seating area features a round table surrounded by four metal chairs. A tall, grass-like sculpture stands nearby, complemented by a wooden railing and a concrete patio. The view of the hills in the background adds to the setting.

4.95 out of 5 average rating, 64 reviews

Your Madison Home Away from Home

While staying in this cozy home, you can enjoy a peaceful morning with a small view of the Ohio River then use the golf cart to explore the historic town. Take a leisurely stroll along the Ohio River waterfront, visit the local winery, or indulge in the local restaurants and cafes nearby. Whether you're visiting Madison for a weekend getaway or a business trip, our home offers the perfect blend of comfort, convenience, and local charm. Book your stay today and make unforgettable memories.

4.99 out of 5 average rating, 226 reviews

The living room features a large sectional sofa facing a wooden coffee table and an electric fireplace. Natural light enters through two windows with light curtains, while a cozy armchair is positioned beside the fireplace, creating a relaxed 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, 142 reviews

A wooden deck overlooks a lush, green landscape with trees and a winding path. A metal planter sits on the deck, offering a space for gardening. Dappled sunlight filters through the leaves, creating a serene outdoor setting.

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 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

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 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.

4.98 out of 5 average rating, 142 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

An indoor pool area is showcased with a bright sky and floor-to-ceiling windows offering scenic views of the surrounding hills. The pool is surrounded by tiled flooring and potted plants, creating a serene setting. Skylights enhance the natural light within the space.

4.98 out of 5 average rating, 120 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 open living area features a cozy seating arrangement with a dark sofa and a light wood coffee table. The kitchen showcases modern stainless appliances, butcher block countertops, and a reclaimed wood island with stools. Sliding barn-style doors lead to an inviting space beyond.

Cottage in Madison

4.9 out of 5 average rating, 182 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.

4.98 out of 5 average rating, 110 reviews

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

209 King Beds, River View, Deck, Parking

Stay at General’s Quarters (209) — a stylish 3-level home in historic downtown Madison! Just steps from the Ohio River, Bicentennial Park, shops, bars, and restaurants. Sleeps 10 with 4 bedrooms & 3.5 baths. Enjoy modern comforts, fast Wi-Fi, a full kitchen, reserved parking and walkable access to festivals and local charm. Perfect for families or group getaways!

4.99 out of 5 average rating, 182 reviews

The cabin features a rustic wooden exterior with a metal roof, surrounded by lush greenery. A wide porch with log railings offers a shaded area, and stairs lead up to the inviting entrance. Multiple seating options can be seen on the porch.

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 warm dining area features a wooden table surrounded by black chairs. Natural light brightens the space, reflecting off the polished wooden floor. A modern kitchen is visible in the background, equipped with stainless steel appliances and light cabinetry.

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.

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House rentals with outdoor seating

A comfortable living room is presented, featuring a large gray sofa and a dark couch, positioned around a wooden coffee table. A TV is mounted on the wall, complemented by a stylish floor lamp. Natural light enters through the windows, illuminating the area.

5 out of 5 average rating, 44 reviews

2 King Beds-1 Block to Main St-Downtown Cottage!

KristopherRating, 5 stars3 weeks ago

We had a great stay at this cozy little house in Madison! The 2-bedroom space was clean, comfortable, and pet-friendly, which was perfect for our trip. It's in a great location—an easy walk to the riverfront, Main Street, and lots of great bars and restaurants. Quiet neighborhood but close to everything. Highly recommend for a relaxing and convenient stay in Madison!

An historic black-and-white photograph depicts a two-story brick building with a sign reading 'Walnut St. Saloon.' In front, a horse-drawn wagon is positioned beside a man sitting on it, while another man stands by the building entrance.

5 out of 5 average rating, 83 reviews

Walnut Street Saloon BNB

BenRating, 5 stars1 week ago

Great place and pleasantly surprised how beautiful the place is. Easy walking to attractions in town. Highly recommend!

A covered porch features a six-seat wrought iron dining set, providing a shaded space for outdoor gatherings. The flagpole displays the American flag against a clear blue sky. Surrounding greenery adds a touch of nature, enhancing the welcoming exterior of the home.

4.95 out of 5 average rating, 59 reviews

Bicentennial Park View

DouglasRating, 5 stars1 week 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!

The exterior of the house features a covered front porch with two wooden chairs and a small table, surrounded by landscaped greenery. A light-colored brick facade is complemented by a black roof and accents. A pathway leads to the entrance, providing a welcoming approach.

4.97 out of 5 average rating, 36 reviews

Annies river house!

AaronRating, 5 stars6 days ago

Everything about the place was great and met our needs. Appreciated the spaciousness and lack of clutter so we had a place to put our personal things.

A historic two-story home features a gray exterior with white columns supporting the porch. Lush green landscaping includes small bushes, with a paved pathway leading to the entrance. A wrought-iron fence encloses the yard, creating an inviting outdoor space.

4.95 out of 5 average rating, 96 reviews

Watchmaker Place in Historic Madison District

BeckyRating, 5 stars1 week ago

I booked this place for a girls' weekend, and we all loved the house. The design, amenities, and location were great—close to Main Street and the Riverwalk. It was clean and well-stocked with everything we needed.. Christopher, the host was responsive and friendly to communicate with. I highly recommend this place to anyone looking for a wonderful space and atmosphere.

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.

5 out of 5 average rating, 21 reviews

The Whitehall Cottage

Michael JosephRating, 5 stars2 weeks ago

Loved the place! Great location and decor was so cute! Would definitely stay there again.

The exterior of the home features a charming blue facade and a welcoming front door with a decorative glass accent. A brick pathway leads to the entrance, bordered by neatly trimmed greenery and potted plants. Lush shrubbery frames the property, enhancing its inviting appeal.

5 out of 5 average rating, 72 reviews

The Book Haven - A Book Lover's getaway near Main

JessicaRating, 5 stars1 week ago

Very cute and clean shotgun style historic home, very comfortable and well appointed. It had everything we needed. Walkable to an adorable downtown. Street parking was not a problem for us. Comfy beds and linens. We loved the backyard and patio for playing cards in the evenings. Host was extremely responsive and helpful, even though we found it that he was on vacation for part of our visit! This a great space, no complaints. Absolutely would book again. Thanks to Chad for having us in his home.

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Apartment rentals with outdoor seating

4.89 out of 5 average rating, 37 reviews

An outdoor area features a circular pool surrounded by a safety fence, with a fire pit situated on a gravel surface. Two blue chairs are positioned near the fire pit, offering a space for relaxation. Lush greenery provides a natural backdrop.

Apartment in Aurora

Family-friendly 2BR Hot Tub & Pool

KittyRating, 5 stars2 weeks ago

Danessa’s place was perfect for our trip, spacious, clean, and very quiet. Our host was always helpful and quick with her response to any questions I had. I would definitely stay here again

A spacious living area is characterized by a dark leather sectional and a wooden coffee table atop a patterned area rug. Light extends from a chandelier, illuminating the open layout that connects to a kitchen with blue cabinetry in the background.

Apartment in La Grange

Prohibition Apt at Pillow and Paddock B & B

SharonRating, 5 stars1 month ago

We rented this space plus the attached pillow and paddock inn for our entire family and it was awesome! The owners go above and beyond to make you feel welcome. The place is fully stocked with everything you need and more. The pigs and horses were also great fun for the kids!

The spacious studio suite features a queen-size bed with a light-colored duvet, accompanied by a comfortable couch. Large windows allow natural light to fill the room. A flat-screen TV is mounted on the wall, and a small dining area with stylish seating is visible.

4.88 out of 5 average rating, 16 reviews

The Regatta Room (Unit 3) - Ohio River Views

JerriRating, 5 stars4 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! 😊

A charming exterior view of the home features a cozy facade with two large front windows framed by wooden shutters. The entrance is adorned with plants and seasonal decorations, while a decorative wrought iron fence adds to the welcoming atmosphere.

4.97 out of 5 average rating, 525 reviews

Dragonfly Suite

LaurenRating, 5 starstoday

The dragonfly suite was the perfect home away from home. After a long day on the road this was the perfect place to land. All the amenities you need, adorable decor, and the comfiest bed! Even though it’s a close knit neighborhood, our space still felt very private. Tammy was a fabulous and communicative host, who obviously puts a ton of thought into the details of her space. Extremely walkable to riverfront, shops, restaurants, bars, etc. Madison is such a cool town! We hope to come back and visit again. Thanks Tammy!

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.

4.98 out of 5 average rating, 244 reviews

Rivers Edge-Historic Hunger House-Upstairs-Madison

StevenRating, 5 stars4 days ago

In our view, this place gets a 10 out of 10. We’re already trying to get back there as soon as possible. The location has perfect walkability and is close to the best of Madison. We Airbnb all over the country and I can honestly say this was the cleanestaccommodations we found is amazing and we wouldn’t think of staying anywhere else. Thank you, Angela!

Superhost

A multi-suite building is displayed, featuring four distinct suites identified by colorful signage. The structure is complemented by a striking red roof and large windows, with well-manicured grass surrounding the property. Trees are visible in the background against a clear sky.

JohnRating, 5 stars4 weeks ago

Sugar Berry ~ Charming Guest House in Madison

This location is very close to downtown but you feel like your way out in the country.

Superhost

A spacious bedroom features a comfortable bed with white linens, complemented by a tufted bench at the foot. Exposed brick walls contrast with sleek modern appliances in the kitchen area, while warm wood flooring and soft lighting create a cozy ambiance.

Apartment in Aurora

4.84 out of 5 average rating, 109 reviews

Studio Apartment w/ Beautiful View!

DebRating, 5 stars2 days ago

The studio was adorable and everything we expected based on the pictures and details provided. The shower is very powerful. The bed is comfortable. It was a super hot, muggy day and the A/C had no problem keeping up. The balcony was nice and convenient for us smokers. Josh was very communicative, friendly and responsive. Stayed here for our 28th anniversary trip. Was perfect for the two of us. Would definitely recommend.