House vacation rentals in Trimble County

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Top-rated house rentals in Trimble County

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Madison

5 out of 5 average rating, 87 reviews

The Row House

Modern flair with antique charm sets this BnB apart! Located on quiet street in the heart of historic downtown Madison, this fully renovated 1830s Row House has you steps away from everything! Whether it's a festival or fall colors, a boat race or car show on the riverfront, a micro brewery or winery, antiquing or historic tour, hiking Clifty Falls or simply just getting away, we have the location for you. *HVAC system includes whole-house air purifier. Max of 4 guests, no children under age 8.

Guest favorite

Home in Madison

5 out of 5 average rating, 89 reviews

The Fashion House on Central

This beautiful historic home is in the heart of downtown Madison. It has been completely renovated with 4 large bedrooms and 3 full baths. This massive home is a show place and winner of the 2019 Historic Madison Inc. Preservation Award. The Fashion House is perfect for your family or friends gatherings with it's grand living and dining room. Madison features more historical blocks than any city in the US. We are also Indiana's Music City! You will be right in the heart of Main Street USA.

Superhost

Home in Madison

4.88 out of 5 average rating, 8 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!

Guest favorite

Home in Madison

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.

Top guest favorite

Home in Milton

5 out of 5 average rating, 29 reviews

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.

Guest favorite

Home in Madison

4.96 out of 5 average rating, 51 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.

Top guest favorite

Home in Bedford

4.99 out of 5 average rating, 209 reviews

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.

Top guest favorite

Home in Madison

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.

Superhost

Home in Madison

4.87 out of 5 average rating, 79 reviews

Corporate housing located along the Ohio River

Beautiful riverfront home. Home is all on one level. Located on a dead end road with other homes that have seasonal renters and some permanent residents. Neighborhood is a mix of newer homes and older homes. Short drive in to downtown Madison. There is a taxi service/Uber in downtown Madison. 25 minutes to Markland dam bridge in Switzerland County IN connecting to Gallatin County KY, approx. 1 hour to Louisville or Cincinnati. Off street parking, 32x12 covered porch with grill.

Top guest favorite

Home in Madison

4.94 out of 5 average rating, 51 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.

Top guest favorite

Home in Madison

4.98 out of 5 average rating, 129 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

Superhost

Home in Madison

4.83 out of 5 average rating, 12 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.