Vacation rentals with outdoor seating in Trimble County

A charming entrance of the home is shown, featuring a maroon-colored exterior and a covered porch. An American flag gently flutters above, while a walkway leads toward the Ohio River visible in the background, framed by trees and a peaceful landscape.

4.97 out of 5 average rating, 39 reviews

River Living - Beautiful Views of the River

Peaceful Retreat or Heart of the Activity There is easy access to all things Madison from this beautifully updated, well furnished, centrally located home Only 2 blocks to Main St shops, dining & festivals Just feet from the Ohio River puts you on the doorstep of the Riverwalk & all festivals on Vaughn Dr Unobstructed, breathtaking views of the Ohio River & Madison Bridge Just 200 ft to public boat ramp & street parking spacious enough for a boat makes this a boaters dream This home has it all!

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

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

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.

Superhost

The exterior of a charming Italianate townhouse is displayed, featuring brick walls and classic black shutters. Red doors are accented with decorative flags, while a well-maintained garden with shrubbery and mulch offers a welcoming appearance. The property is illuminated by natural sunlight.

Townhouse in Madison

4.84 out of 5 average rating, 25 reviews

"Madison Manor II” *Regatta Special* Great Patio

*Regatta Special* 2 local growlers chilled & ready +Noon check in +Late check out! This spacious Italianate style townhouse is nestled in the heart of downtown Madison just 2 blocks from the river. Rent a golf cart & live like a local! House is beautifully furnished with ample amenities for optimal guest comfort & convenience. The decor reflects the rich steamboat history of the city. Home adjoins Madison Manor I which can be booked separately. Shared patio with hot tub, fire pit, gas grill.

5 out of 5 average rating, 29 reviews

The cabin exterior features a log construction with a sloped roof and a welcoming porch area. Several sturdy chairs are positioned on the porch, surrounded by neatly trimmed landscaping and a gravel pathway. Nearby trees provide a sense of tranquility to the outdoor space.

Home in Milton

The Madison-Milton Cabin

Welcome to the Madison Milton Cabin. Enjoy a unique, peaceful setting just 5 minutes from Downtown Madison. Enjoy the great shopping, dining, and entertainment and finish your day relaxing next to a cozy outdoor fire. If you love sunsets you will love the views from the cabin. The house features a loft bedroom with comfy adjustable bed. The bathroom includes an oversized soaking Tub/Shower and the main living room includes a queen size pull out couch. Stay connected with high speed internet.

4.99 out of 5 average rating, 215 reviews

A light-filled dining area features a wooden table surrounded by white chairs. A blue area rug anchors the space, complemented by a chandelier above. A kitchen bar with seating is visible in the background, and large windows provide views of the surrounding trees.

Home in Bedford

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 160 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

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

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

Welcome to The Regatta Room by Parker Places! This luxury studio suite is recently remodeled and features brand new everything. It comes stocked with a full eat-in kitchen, new appliances, one queen-size bed, a comfy couch, TV, WiFi, and more. PRIME location with a view of the Ohio River, instant access to the walking path along the river, close to shops, cafes, & restaurants. PERFECT location for anything downtown, and it is just steps away from Madison's famous Regatta event.

5 out of 5 average rating, 66 reviews

An oversized clock sculpture adorned with the phrase 'OFF THE CLOCK' is featured in the foreground. Surrounding landscaping includes planters with various plants. The riverfront property is visible in the background, complemented by a deck and string lights overhead.

Guest suite in Hanover

OFF THE CLOCK River House

OFF THE CLOCK RIVER HOUSE is a rare find among Air BnB options. Our riverfront property is ideal for ALL water activities; boating, jet skiing, kayaking, fishing, and swimming. A private concrete launching ramp and a large dock with a double jet ski dock are located directly in front of our home. Of course, you can also enjoy the gentle flow of this peaceful, riverside escape allowing yourself to unwind and recharge. Historic Madison offers many options to explore.

4.98 out of 5 average rating, 170 reviews

The cabin features a rustic exterior with a warm wooden facade and a distinct red metal roof. A wide porch wraps around the front, complemented by natural wooden railings. Large windows provide ample light, and the surrounding greenery adds to the serene atmosphere.

Cabin in La Grange

Running Creek Log Cabin

Our cabin is about 6 miles to dock your boat onto the Ohio River. A 15 minute drive into downtown Lagrange for more shopping including food and boutiques. We are 30 drive into Louisville and 1 hour 15 min. drive to Cincinnati Ohio. It is on a 5 acre property and attached by a driveway to a home that we call Southwest Retreat that is on airbnb and 5 acres. We have a security camera on the outside of the house on the front porch facing the driveway.

4.99 out of 5 average rating, 138 reviews

A spacious great room features reclaimed barn wood flooring and a stone fireplace as its focal point. Large windows allow natural light to fill the space, complemented by rustic furniture, including comfortable armchairs and a wooden coffee table. Warm tones create a cozy gathering area.

Farm stay in Pendleton

Fossil Creek Woodlands...Rustic, Private, Retreat

Fossil Creek provides a rustic relaxing environment for family and friends to escape the hustle and bustle of every day life and enjoy beautiful Kentucky woodlands. Our home is situated at the base of 65 wooded acres in Oldham County Kentucky. Its name comes from the plethora of fossils that can be seen in the creek that runs along the front of the property. Our place is great for couples, families, reunions, retreats and church groups.

4.88 out of 5 average rating, 8 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.

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House rentals with outdoor seating

The exterior of the property features historic architecture with large, elegant windows. Decorative elements are visible along the façade, and potted plants are placed outside the entrance. The vibrant colors of the building contrast with the greenery of the surrounding trees.

5 out of 5 average rating, 15 reviews

The Magnolia on Main hosted by Swell Stay

JenniferRating, 5 stars4 days ago

When I was growing up in Madison, I always wondered what it would be like to live above one of the Main Street stores. The Magnolia on Main finally gave me that experience. Over the years we have stayed in many inns and B and Bs near Madison, but this is our new favorite! It’s beautiful, spacious, spotless, and well equipped. Everything we might want to eat or do is within walking distance. We can’t wait to go back!

A view from the porch showcases the Ohio River, framed by leafless trees and rolling hills in the distance. A rope railing lines the edge, while a small round table and a chair are positioned in the foreground, inviting relaxation.

5 out of 5 average rating, 13 reviews

Riverside Retreat 2 - Steps to the River & Main St

HeatherRating, 5 stars2 weeks ago

The home was spacious and very well kept. It was decorated well and felt homey from the moment we walked in. We love the closeness to downtown because we like to walk everywhere in Madison. Our host was very responsive and friendly. There was a lovely snack basket and some custom mugs for us to keep. It is those small touches that really make guests feel welcome. We can’t wait to visit again!

5 out of 5 average rating, 15 reviews

An outdoor living area features a stone fire pit surrounded by several seating options. The landscape includes green grass, and the view of the river is visible in the background, complemented by a clear blue sky and scattered clouds.

Home in Bethlehem

1872 Bethlehem Home w/ View of Ohio River!

Linda DRating, 5 stars1 month ago

This was our third time staying at this beautiful historical, peaceful home. Great place to walk or bike and sit on the porch and watch the barges go by.

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

The exterior of a charming shotgun house is displayed, featuring exposed red brick and whitewashed walls. Two framed windows are symmetrically positioned on either side of a central door, while a flag adds a touch of character. Lush greenery is visible in the foreground.

4.98 out of 5 average rating, 41 reviews

Carpet Alley

KelliRating, 5 stars2 weeks ago

Absolutely wonderful place. My son and I had a wonderful time visiting the city . Beautiful,clean and so charming. We will definitely be back again.

A spacious living area features light blue walls and a comfortable sectional sofa. Natural light flows through the large windows, illuminating the room. An area rug with floral patterns lays on the hardwood floor, complemented by artwork depicting animals on the walls.

4.95 out of 5 average rating, 43 reviews

The Nature House

StephanieRating, 5 stars2 months ago

Jennifer’s place was a perfect stay for our family of seven. We had a kid with us and one of the rooms upstairs is connected to another room that has a futon. There isn’t a door that separates the two rooms but we were fine with that. It was sunny and nice to be able to sit on the back patio. We rented a golf cart and took that around town (designated areas). The town is very walkable and in the summer months, with everything open, I can imagine it being lively. We took a walk along the Ohio River (which we walked to) and that was nice. Kitchen also had what we needed to make meals. We would definitely stay here again.

A welcoming living area features polished hardwood floors and large windows draped with golden curtains. A modern cream sofa is complemented by colorful accent pillows, while a cozy armchair and a stylish desk provide additional seating. A decorative fireplace adds character.

5 out of 5 average rating, 89 reviews

The Row House

AngieRating, 5 stars1 month ago

We’ve traveled all over the world (even to London & Paris, just like the themed rooms 😉), and this is one of the best Airbnb’s we’ve ever stayed in! Hilary’s attention to detail & thoroughness is amazing! The beds are super comfortable, the shower is wonderful, and we loved the fire bowl in the back! The location is unmatched- perfect for walking to the shops & restaurants nearby and a very short drive for hiking at Clifty Falls! We loved dinner at Red on Main (the dates appetizer was Michelin-star worthy) and seeing live music both nights at Mad Paddles Brewstillery (worth going for their beer wall and their ranch (best I’ve ever had!) alone! We also loved the 12,000 step hike we did at Clifty Falls- some of the most stunning views in Indiana! 🙂 Hilary & Tony’s Airbnb is the best of the best!

4.94 out of 5 average rating, 18 reviews

Little Pink House - South

LeviRating, 5 stars1 month ago

The little pink house was an incredible place to stay. The cleanest Airbnb I’ve ever stayed at. Location was incredible to downtown and the river. Ashton and Addison went above and beyond when I asked for their help on a birthday surprise upon arrival. Great host and great spot. If I come back to Madison this is where I’ll be staying.

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Apartment rentals with outdoor seating

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!

GabrielaRating, 5 stars1 week ago

we celebrated our 10 yr anniversary. we wanted seclusion and peace and thats what we got! the indoor pool is connected to your room the giant windows allowed for a clear view of the beautiful surroundings. pool was super clean and well maintained the hot tub was the same. Sandy is an incredible host and we have plans of returning every yr to celebrate our anniversary ❤️

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!

Superhost

A neatly arranged row of four suites is displayed on a single-level building with a red roof. Each suite is labeled, showcasing distinct names: Sugar Maple, Sugar Berry, Sweetbay Magnolia, and Sweet Gum. Surrounding trees and a clear sky provide a natural backdrop.

RyanRating, 5 stars24 months ago

Sugar Maple ~ Charming Guest House in Madison

Love the place! 5 mins to downtown Madison and the river. The place was just as described, great amenities, clean, picturesque and had a cute very friendly cat outside

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, 524 reviews

Dragonfly Suite

DanielleRating, 5 stars4 days ago

Great spot for my husband and I to stay in Madison. Easy to walk to the Main Street attractions, the riverfront, and a short drive to Clifty Falls State Park. Loved the space!

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.

A cozy living area is highlighted by a large sectional sofa adorned with patterned throw pillows. A round wooden coffee table sits at the center, featuring a decorative tray with a glass vase and a lamp. Natural light filters through multiple windows with light blinds.

Apartment in Prospect

Acadia in the Commons

GregRating, 5 stars2 months ago

This property and the host and family ARE AMAZING!!!!!! They were very accommodating, flexible, kind, responsive, and most importantly the property IS AS DESCRIBED and more! You seriously can beat the Norton's Common area! There is a lake 1 block away, a connected bakery, and tons of playground areas for kids! The wrap around balcony is a amazing touch! We will definitely be returning soon!

A serene morning scene captures a misty landscape as early sunlight begins to rise over a forested area. Layers of fog gently blanket the trees, with soft hues of orange and blue filling the sky, creating a tranquil atmosphere.

GerardoRating, 5 stars5 months ago

Pleasant Ridge Bliss

Great place will be back