Vacation rentals in Henry County

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Top-rated vacation rentals in Henry County

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Top guest favorite

A narrow staircase with wooden steps leads downward, flanked by a stone wall on one side. The natural texture of the stone contrasts with the smooth wood, while a black railing provides support. The descent opens to a light-colored doorway at the bottom.

Cabin in Louisville

5 out of 5 average rating, 214 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favorite

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

4.99 out of 5 average rating, 215 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

Two wooden rocking chairs are positioned on a wooden deck, facing a large window that overlooks a natural setting filled with autumn foliage. A grill is seen nearby, and fallen leaves cover the ground, adding to the tranquil outdoor environment.

Cabin in Vevay

4.98 out of 5 average rating, 109 reviews

The Cabin

As you walk in, The Cabin wraps it's arms around you and says " Welcome home." You can feel the stress leave you as you settle in for your stay at this scenic cabin on 9.8 wooded acres. Fully furnished, spacious 1 room cabin with stone wood burning fireplace, equipped kitchen, bath with shower and twin over queen bunk bed. Refresh your mind & soul on the covered back porch overlooking the mature woods. Enjoy watching the abundant wildlife, including turkeys, deer, chipmunks and squirrels.

Guest favorite

An aerial view of a sprawling 200-acre farm reveals rolling hills and lush greenery. Several buildings, including a large barn and distinct cabins, are spread across the landscape, surrounded by trees. A winding road leads to the structures, emphasizing the farm’s expansive and serene setting.

Cabin in Owenton

4.86 out of 5 average rating, 433 reviews

Vintage Container Cabin on Beautiful Farm Near Ark

Discover the festive charm of our fully renovated container cabin, nestled along the wooded ridge of our farm. Enjoy the crisp winter air as you explore 200 acres of beauty, or relax by the fire with a glass of local Kentucky bourbon. The cabin features a custom-built design with treasures from around the farm, blending vintage charm of Kentucky's past. Grill up a holiday feast, cozy up on the memory foam mattress, and soak in the beauty of winter from the comfort of your own cozy cabin.

Top guest favorite

A carton containing ten eggs is displayed. Each egg varies in tone, ranging from light beige to brown. The carton is made of recycled material and includes nutritional information printed on the top.

Farm stay in Glencoe

4.96 out of 5 average rating, 131 reviews

Carriage House w King bed, Lux bath, amazing views

Take in the views at this unique and tranquil getaway. This home is part of our beautiful 50-acre working farm where you can regularly see wildlife and heritage breed farm animals. And although it sits nestled on the back ridge, it is also just a short drive to many of Kentucky and Cincinnati's amazing sites. Our farm values caring for earths resources, so we have intentionally created this space with solar power, and toxic free cleaning products. (note: 2nd bed is a deluxe airmatress)

Guest favorite

An open space features a large glass garage door adorned with a view of greenery, allowing natural light to fill the area. Two metal stools are positioned at a small wooden bar against the wall, providing a cozy spot for relaxation or meals.

Treehouse in Georgetown

4.93 out of 5 average rating, 224 reviews

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

Top guest favorite

The image captures a street view of a charming downtown area, lined with brick buildings and shops. A modern vehicle is parked along the sidewalk, which is illuminated by natural light. Decorative string lights are visible overhead, enhancing the inviting ambiance of the setting.

Tiny home in La Grange

4.98 out of 5 average rating, 221 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Guest favorite

Home in La Grange

4.93 out of 5 average rating, 111 reviews

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

Top guest favorite

Cottage in Pleasureville

4.99 out of 5 average rating, 214 reviews

Tiny House Farm Stay on One Goat Farm

This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery. Located in the heart of an Amish community. We breed, show and raise registered myotonic goats. We have a fall and spring kidding season so if you book during that time, expect to see baby goats frolicking in the fields. The cottage is on a functioning farm with horses, cats, goats and a donkey. We offer overnight housing facilities for your own equines as well.

Guest favorite

A well-defined pathway is illuminated by small lanterns, guiding guests toward the cottage nestled among trees. The gentle glow from the lights contrasts with the surrounding dusk, creating a serene approach to the inviting space.

Guesthouse in Shelbyville

4.97 out of 5 average rating, 112 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Top guest favorite

A serene view of lush green trees stretches out, showcasing the natural landscape and rolling hills. The image captures the vibrant foliage under a partially cloudy sky, creating a peaceful atmosphere within the secluded setting.

Apartment in Madison

4.98 out of 5 average rating, 123 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Top guest favorite

A rustic tiny house, built with natural wood, is set among lush greenery. A stone fire pit is surrounded by an open yard, with a wooden picnic table positioned nearby. Smoke rises from the fire, adding to the serene outdoor ambiance.

Tiny home in Frankfort

4.98 out of 5 average rating, 402 reviews

Tiny Home with Huge Charm near the Elkhorn Creek

Just minutes from downtown Frankfort, this place is a little peaceful country getaway with a lot to offer! It’s nestled on a quiet street with great access to the beautiful Elkhorn Creek! If you’re into Bourbon tours, Horses, canoeing/kayaking/fishing, or Natural and Historical sites, this place is a great location in the middle of a lot to see and do! The tiny house has a small kitchen and bath as well as a yard and private patio and grill to enjoy!