Vacation rentals in Trimble County

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.

4.99 out of 5 average rating, 239 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

4.89 out of 5 average rating, 9 reviews

Riverside Retreat - Steps to the River & Main St

Newly remodeled, well furnished, spacious home in the heart of everything going on in historic downtown Madison, Indiana. Steps from the river puts you on the doorstep of the Riverwalk and all the festivals on Vaughn Dr. Just 2 blocks to Main St makes an easy walk to all of the shopping, dining and festivals on Main St. Views of the Ohio River and Madison bridge are beautiful from the front and back of this home. Close to the public boat ramp and ample room for boat parking. Come stay with us!

The spacious interior showcases high wooden beams and a warm, inviting light. A dining table is positioned under the beams, with black chairs and a decorative centerpiece. Kitchen appliances can be seen in the background, enhancing the open-concept layout.

5 out of 5 average rating, 25 reviews

Livery Loft: BEST location!

This beautiful loft apt is spacious and guests say "it's beyond amazing"! 2+ bdrm 2 luxury bathrooms offer SO many amenities you won't want to leave! It has a very spacious living room, dining room & gourmet kitchen. The master bath has a fireplace above the soaking tub & a massage shower. The other bath has a rainfall shower and heated toilet seat: add luxury linens & you will feel very pampered! We have the best location just off main street and 3 blocks from the relaxing riverwalk.

A stylish black door marks the entrance, adorned with a decorative lantern and a whimsical horse figure. Lush ferns are housed in tall planters on either side, complementing a welcome mat at the foot of the door.

5 out of 5 average rating, 305 reviews

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”.

4.95 out of 5 average rating, 42 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.

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.

4.96 out of 5 average rating, 55 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, 210 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, 329 reviews

A serene view of a riverbank is shown, with a gently flowing river bordered by lush green hills. A lamppost stands on the pedestrian path, providing illumination. The scene captures the tranquility of the area, inviting exploration and relaxation by the waterfront.

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.

4.97 out of 5 average rating, 29 reviews

Main Street Retreat Prime Location 3 Bedroom Top1%

Enjoy a relaxing experience at this centrally-located historic home. The Retreat offers an opportunity to immerse yourself in the beauty of Madison's historic district, all while enjoying the comforts of a home away from home. The 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 girl's trip, weekend getaway book your stay today and create lasting memories.

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, 133 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 exterior of the triplex features two levels with a light grey facade and contrasting red doors. A staircase leads to a balcony with seating, while gravel surrounds the building. Lush greenery and a hillside are visible in the background.

4.86 out of 5 average rating, 14 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.