Vacation rentals in Trimble County

5 out of 5 average rating, 146 reviews

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.

Apartment in Madison

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 covered patio area is equipped with a dining table and six chairs, surrounded by greenery and trees. A charcoal grill is positioned nearby. Decorative plants are placed on the table, and a wooden bench with cushions complements the outdoor space.

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.

5 out of 5 average rating, 306 reviews

Two candle holders with a rustic design are mounted on a light-colored wall. Each holder features a lit candle wrapped in burlap. Nearby, a sprig of greenery adds a natural touch to the setting.

Apartment in Madison

Stablemaster’s Quarters/ Best downtown location!

The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, a laundry room and a furnished white kitchen will all be appreciated. Carefully, the historic charm is blended within. You will soon see why the entire building is award winning! This fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the Midwest”.

5 out of 5 average rating, 29 reviews

A cozy corner features a cast iron gas fireplace, set against a rustic stone wall. The fireplace is positioned on a circular brick platform, providing warmth to the surrounding wooden interior. A decorative wall hanging adds character to the natural wood finishes.

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.

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

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.

4.99 out of 5 average rating, 214 reviews

A spacious home is visible, framed by greenery and a gravel pathway. Several outdoor chairs are arranged around a fire pit, while the deck features a covered seating area. The two-story structure showcases large glass windows, inviting natural light into the interior.

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.

4.86 out of 5 average rating, 332 reviews

A private deck is presented with wooden railing, featuring a blue umbrella and several black folding chairs. A textured area rug covers part of the deck, creating a comfortable outdoor space with a view of surrounding buildings and the sky.

Loft in Madison

Historic Madison Spa Retreat perfect location

Highlighted on Madison Loft Tours. 1800s historic 3rd story charming Loft offers a spa retreat & private deck. In the midst of Madison’s shopping, dining, festivals & nightlife. Located between Main St and the river. Antique furnishings and beautiful woodwork highlighted. Sip local coffee from our private deck or relax in a jacuzzi tub after touring the sights. Wineries, bars, Mad Paddle Brewery and great restaurants surround us. Hanover College & Clifty Park are minutes away.

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

4.98 out of 5 average rating, 170 reviews

A spacious kitchen area features wooden log walls and modern pendant lighting. An island with a granite countertop and a double sink is highlighted. A dining table is positioned in the corner, with sliding glass doors leading to the outdoor view.

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, 137 reviews

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.

4.97 out of 5 average rating, 157 reviews

The Crafty Fox Den - Retreat House

Nestled in Madison, Indiana’s beautiful historic district. The home is a newly renovated four square craftsman, located in the middle of town, still quiet and cozy. You are a half of a block from Main Street, the beautiful Broadway fountain, and just three blocks from the river, Lanier Mansion, and Crystal Beach, Visitor’s Center and within walking distance of all of Madison’s event locations as well as historic properties.

The exterior of a cozy cottage is showcased, featuring a light green brick facade. A short set of stairs leads up to the front door, complemented by a black railing. The surrounding area includes black mulch and shrubs, with blue skies visible above.

4.96 out of 5 average rating, 28 reviews

Coming Home Cottage

Welcome to Coming Home Cottage, your charming retreat in the heart of historic downtown Madison, Indiana. This cozy cottage offers the perfect home away from home, located only one block from Main Street and easy access to all of downtown Madisons many shops and festivals, while being just minutes away from the modern Madison hilltop. Come and enjoy a short stroll to all Madison has to offer.

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Other great vacation rentals in Trimble County

5 out of 5 average rating, 13 reviews

The Magnolia on Main hosted by Swell Stay

JulieRating, 5 stars1 week ago

We had a fantastic stay! The home is absolutely stunning—beautifully decorated with so many thoughtful touches that made it feel extra special. The beds were super comfortable, and having 3 full bathrooms made it easy for the 9 of us to get up and out in the mornings. The hosts were the best—great communicators and very responsive. The location couldn’t be better, right in the heart of Madison. It was the perfect getaway to relax, sip some wine, shop, and make amazing memories with the girls. Highly recommend!

4.97 out of 5 average rating, 36 reviews

The image captures a serene riverside scene with a view of a large white bridge spanning across the Ohio River. Lush green grass lines the riverbank, and the water reflects the clear blue sky dotted with a few clouds. The surrounding landscape features gentle hills in the background.

Cottage in Madison

Cheerful 3-Bedroom cottage with fireplace.

LoriRating, 5 stars2 months ago

The house and location were beautiful and Brian was incredibly helpful and responsive. We can’t wait to come back!

Campsite in Pendleton

4.86 out of 5 average rating, 49 reviews

Camping at Hones Pointe campground and park

SeanRating, 5 stars22 months ago

Oh, nothing about the property was bad. I really appreciated the early check-in, but I was just unclear on what spots were available or if they were reserved. So I took a chance and I hope I did not cross any lines. The river was beautiful, the spots were well-maintained, I only wish they had electric at the place that I chose. It did have outlets but no electric hook ups. All in all a great stay and I will come back just to relax.

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 stars3 weeks 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.