House vacation rentals in Trimble County

5 out of 5 average rating, 93 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.

4.96 out of 5 average rating, 45 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!

4.96 out of 5 average rating, 23 reviews

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.

5 out of 5 average rating, 92 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.

4.99 out of 5 average rating, 103 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, 32 reviews

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.

5 out of 5 average rating, 26 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!

4.96 out of 5 average rating, 72 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, 218 reviews

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.

4.9 out of 5 average rating, 48 reviews

Historic Madison on Main Street

If you want to be in the heart of Historic Madison this is the place for you! Right on Main Street, this home built in 1860, has 3 bedrooms, 2 bathrooms, and nearly 2,000 sq. ft. It's newly renovated yet has all the character of a mid-1800's home. It sits on the 2nd story just above The Attic Coffee Mill Cafe, which just won an award as the best coffee and cafe in Madison. You can wake up each morning and brew your own coffee or just come downstairs to join us for coffee and breakfast.

4.91 out of 5 average rating, 70 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.