Vacation rentals with a patio 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, 38 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!

4.89 out of 5 average rating, 9 reviews

A multi-level house is situated on a hillside, offering a wide deck with railings and large windows. Surrounding greenery and shrubs are visible, complementing the natural landscape. A clear blue sky serves as the backdrop, enhancing the peaceful ambiance of the property.

Home in Hanover

T&E Riverhouse Retreat

Experience the perfect blend of relaxation and recreation at our stunning property with panoramic river views. Enjoy direct beach access, where you can soak up the sun, swim, fish, kayak, and more. The home features upper/lower decks, a basketball goal, fire pit, and a kitchen on each level. Whether you're here for a peaceful getaway or an action-packed vacation, this riverfront retreat has everything you need for an unforgettable experience. Book your stay today and create lasting memories.

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, 88 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.

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

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.

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, 14 reviews

The Magnolia on Main hosted by Swell Stay

Featured on the Magnolia Network, this 1800’s property has been lovingly restored by the Beck Family. This 3 bedroom, 3.5 bath luxury residence has been thoughtfully designed with the Madison tourist in mind. Enjoy the view of the Main St parade from the 2nd and 3rd floors or spend time on the balcony watching the sun set on the majestic Ohio River. Centrally located on the Golden Block of Main Street in downtown Madison Indiana, you couldn’t stay in a more ideal location. Come stay awhile!

The exterior of a modern two-story house features a dark blue brick facade, accented by large arched windows. A wooden entrance is framed by a covered porch, leading to a well-maintained landscaped area with tidy gravel, small shrubs, and ornamental plants.

4.97 out of 5 average rating, 61 reviews

Glenda’s Overlook

Situated just one and a half blocks from the iconic Milton-Madison Bridge spanning the picturesque Ohio River, Glenda's Overlook offers the perfect retreat for you and your loved ones. Our home is located merely a few walking blocks, or short golf cart ride, from the historic district, and offers easy access to the city's charming wineries, shops, restaurants, Crystal Beach and vibrant festivals that Madison has to offer. Additionally, we are only a short drive to Clifty Falls State Park.

A charming shotgun style home features a light blue exterior with white trimming and a covered front porch. The porch is adorned with plants and a small seating area. A pathway leads to the entrance, framed by a neat garden and wrought iron railing.

4.93 out of 5 average rating, 30 reviews

The Baltmore

Experience the charm of an 1800's shotgun style home in Madison's National Historic District. This home was completely remodeled yet maintains its historic character. All of the artwork and decor was purchased locally and pays homage to Madison and its vibrant arts community. Located in a quiet neighborhood yet just a few walkable blocks away from the heart of downtown Madison's shops, restaurants and lively music scene. Perfect for a small family, couples or girlfriend getaway.

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

New June 2024! Full time Airbnb. Come stay at this newly renovated home in historic downtown Madison. This 3-bed/2-bath home is adjacent to Bicentennial Park and includes a fully stocked kitchen, washer & dryer, internet, keyless entry, front porch that overlooks the Ohio River and more. From the front porch of this home, enjoy the festivities of live concerts and Friday-night movies. You will enjoy easy access to everything Main Street offers from this centrally located home.

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.

4.87 out of 5 average rating, 15 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.

4.93 out of 5 average rating, 28 reviews

A charming brick townhouse is displayed, with contrasting black shutters and red doors. Decorative elements, including patriotic wreaths and bunting, adorn the windows. Lush greenery and a mulched garden area add to the inviting exterior, complemented by a clear blue sky above.

Townhouse in Madison

"Madison Manor I” Special Book 2 nights Get 1 Free

*JUNE SPECIAL* - Noon check in -S’mores -Local wine -Buy 2 nights, get one FREE -Late check out This spacious Italianate townhouse is nestled in the heart of downtown Madison just 2 blocks from the river. The house is beautifully furnished with ample amenities for optimal guest comfort & convenience. The decor reflects the rich train history of the city. The home adjoins Madison Manor II which can be booked separately. Shared patio includes hot tub, fire pit, gas gril

Farm stay in Campbellsburg

The image showcases the Tiny Home surrounded by a vibrant garden. Lush vegetation and vegetables flourish in neat rows, while the home sits in the background beneath a partly cloudy sky. A well-maintained lawn and distant structures enhance the rural setting.

5 out of 5 average rating, 32 reviews

Tiny Home in Amish Country

Our Tiny Home sits on our farm called, Tenacity. It is a separate home attached to our home by a wrap around porch. The Tiny House is 800 sqft located on 70 rolling acres of north central Kentucky. This farm has a rhythm that will slow your heart rate, clear your lungs, and revive your spirit. Fireflies light your summer evening under the night sky. Amish families in their black buggies smile and greet you as you pass them on the road. LGBTQ+safe zone

A spacious covered porch features wooden flooring and sturdy beams, providing an unobstructed view of the river and surrounding landscape. A table and several chairs are arranged for seating, while a ceiling fan is installed overhead for airflow.

Home in Milton

5 out of 5 average rating, 4 reviews

The Porch at Milton

Escape to our charming 2-bedroom house, nestled along the serene banks of the river in Milton, KY. Whether you're looking to unwind or explore, this cozy home offers the perfect balance of comfort and nature's beauty. Best of all, you're just a 2-minute drive or a scenic 25-minute walk from the historic and charming downtown Madison, Indiana. Explore local shops, dine at unique restaurants, or stroll along the riverfront.

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Apartment rentals with a patio

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, 119 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

GabrielaRating, 5 stars3 days 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 stars3 weeks 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 stars23 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

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 stars3 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 modern kitchen features white cabinetry and a spacious island with seating for five. The countertops are finished in light stone, complemented by a neutral backsplash. Large windows provide natural light, and stainless steel appliances are neatly integrated into the design.

Apartment in Prospect

Cozy Getaway at Norton Commons!

PaigeRating, 5 stars3 weeks ago

A little difficult to find due to being on the side but after locating everything was perfect!

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

Superhost

The exterior of a single-level guesthouse structure features four separate suites, each with distinct signage. The building has a red roof and dark wood paneling, surrounded by a grassy area and mature trees, creating a welcoming and serene setting.

HeatherRating, 5 stars11 months ago

Sweet Gum ~ Charming Guest House in Madison

Cozy, quiet space just 10 minutes from downtown. Enjoyed the nature aspect and Dugan the resident kitty :). Michelle was a great host and made sure our stay was everything we needed it to be.

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House rentals with a patio

A spacious living room features a comfortable sofa and armchairs arranged around a wooden coffee table, accented by a decorative area rug. A flat-screen television sits atop a wooden console, while a decorative clock artwork is displayed on the wall. Wood flooring adds warmth to the space.

4.93 out of 5 average rating, 130 reviews

Cozy 3 bedroom home, steps away from Main Street

KimberlyRating, 5 stars2 weeks ago

We had a great stay! The location is great and close to many shops and restaurants. The mattresses are FIRM. That was our only small let down as we didn’t sleep very well, but otherwise it was an excellent weekend trip.

4.9 out of 5 average rating, 101 reviews

The living area features a spacious sectional sofa arranged around a round wooden coffee table. Natural light filters through sheer curtains, illuminating the room. Decorative shelves are mounted on the walls, and a ceiling fan is present for comfort.

Home in Crestwood

12 Guest/Top Area /Families/Park

KarenRating, 5 stars2 weeks ago

This home was as described, had plenty of room, and was comfortable. It has the necessities for a good stay. Jennifer was very responsive and helpful. Good value considering how many guests the house can accommodate. The neighborhood is large, but quiet.

5 out of 5 average rating, 107 reviews

A welcoming entryway is presented with soft lighting and decorative accents, inviting guests into the home. An open kitchen area features a spacious island with bar seating, while modern appliances complement the warm cabinetry. A cozy living room showcases comfortable seating, a fireplace, and calming decor. The serene master bedroom includes a large bed, warm colors, and natural light from nearby windows.

Home in Prospect

Stay@Peppermint Cottage Norton Commons w/breakfast

BetsieRating, 5 stars2 weeks ago

Amazing stay. Nicole was super responsive and over the top helpful with info and recommendations. The house was beautiful. Everything exceeded our expectations. Looking forward to coming back !

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

GlenRating, 5 stars3 weeks ago

We had a wonderful stay at Jordan’s place! The house was incredible—spacious, spotless, and thoughtfully prepared for guests. We especially loved the beautiful view overlooking a pond and horse pastures—it was so peaceful and relaxing. The location was perfect for us, with easy access to Hanover College, which made attending graduation weekend smooth and stress-free. Jordan was a great host, and we would absolutely stay here again. Highly recommended!

4.98 out of 5 average rating, 163 reviews

A charming farmhouse features a light yellow exterior with white trim and a welcoming front porch. Lush green grass surrounds the home, and colorful flowers can be seen near the entrance. A flag hangs by the porch, adding to the inviting presentation.

Home in Pewee Valley

Bourbon Trail*Pewee Valley *HOT TUB

SabrinaRating, 5 stars1 month ago

We had a great stay. Hung out in the screened in front porch, grilled, enjoyed the hot tub and the old Derby style of the KY home. Toni was a great host and responded quickly.

4.97 out of 5 average rating, 95 reviews

The exterior of the home features brick siding with white trim and dark blue shutters. Lush green grass surrounds the property, complemented by mature trees. A set of steps leads to the front door, which is framed by small hedges on either side.

Home in La Grange

The Squirrel's Nest - 3 bedroom house with hot tub

LindseyRating, 5 stars1 month ago

Amazingly quaint little cottage. Couldn’t have asked for a better place to stay for our time in Kentucky. Will definitely keep this on our list to stay the next time. Thank you Robin!

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, 63 reviews

Your Madison Home Away from Home

MarkRating, 5 stars1 week ago

We had a really nice stay. Chrissy gave very timely and accurate instructions for checking in and entry was very easy. The "shotgun" style home, an architectural style which is an element of Madison's history, was comfortable and located in a quiet part of Madison. A little bit of a walk from downtown, but the golf cart which was provided for our use made getting to/from downtown fun and easy. In fact riding the cart into town and down along the park and river was one of the highlights of our visit to Madison. Our grandchildren visited us while we were there and they loved the house...and the yard and deck were very handy for playing with them outside. We definitely enjoyed ourselves and felt at home during our stay. Thanks, Mark and Kay

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.