Holiday rentals in Trimble County

5 out of 5 average rating, 146 reviews

Flat 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.

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

Flat 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

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.

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

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, 333 reviews

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.

4.98 out of 5 average rating, 142 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

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.

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 holiday rentals in Trimble County

5 out of 5 average rating, 15 reviews

The Magnolia on Main hosted by Swell Stay

JenniferRating, 5 stars2 days ago

When I was growing up in Madison, I always wondered what it would be like to live above one of the Main Street stores. The Magnolia on Main finally gave me that experience. Over the years we have stayed in many inns and B and Bs near Madison, but this is our new favorite! It’s beautiful, spacious, spotless, and well equipped. Everything we might want to eat or do is within walking distance. We can’t wait to go back!

4.97 out of 5 average rating, 36 reviews

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 stars23 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

Home in Bethlehem

1872 Bethlehem Home w/ View of Ohio River!

Linda DRating, 5 stars1 month 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.

4.95 out of 5 average rating, 43 reviews

The Nature House

StephanieRating, 5 stars2 months ago

Jennifer’s place was a perfect stay for our family of seven. We had a kid with us and one of the rooms upstairs is connected to another room that has a futon. There isn’t a door that separates the two rooms but we were fine with that. It was sunny and nice to be able to sit on the back patio. We rented a golf cart and took that around town (designated areas). The town is very walkable and in the summer months, with everything open, I can imagine it being lively. We took a walk along the Ohio River (which we walked to) and that was nice. Kitchen also had what we needed to make meals. We would definitely stay here again.

4.81 out of 5 average rating, 52 reviews

Home in Vevay

Little Lamb Retreat at the river

RhondaRating, 5 stars1 week ago

This was the ideal place for a relaxing few days we needed. Couches and beds were very comfortable, the view from the porch, beautiful, and of course as others have mentioned, great hot tub! The whole place was very clean.

Tiny home in Milton

4.75 out of 5 average rating, 130 reviews

The Rustic River Retreat.

EdRating, 5 stars3 weeks ago

Nice little place sitting on the Ohio River. Local Neighbors were very friendly. Had a nice fire and view. Easy access to Madison (5 minute drive to most restaurants) several grocery stores in area if your cooking in. House is a tiny house so be aware. Hot shower Kitchen had everything needed to make meals. Bring firewood Or scavenge driftwood. Google Maps had trouble with the address but got us close enough to find it visually.