Holiday rentals in Henryville

Patio Home Charlestown State Park & River Ridge

Welcome to your 5 star super host home away from home! This spacious patio home sleeps 7 guests & includes free parking for 2 vehicles, 2 full baths & a fully equipped kitchen. Located in a quiet, relaxing neighborhood just 20 min from the Louis Muhammad Ali Int’l Airport, min from Charlestown State Park & River Ridge Commerce Center. Perfect for professionals & contractors. It’s the perfect place to relax while enjoying the comfort & privacy of your own home with fast Wi-Fi & cozy furnishings.

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

Comfort de Casa

Our cozy home, set in a quiet neighborhood with safe streets for walking/running, is just a 15-minute drive from Louisville. With a full kitchen, dining room, and spacious living room, this three-bedroom home is great for families or couples to stay comfortably! The full house is available for guest use, except for a few locked closets. Enjoy the new four-seasons room and deck!! House rules: —No more than three vehicles —No parking on street! —Quiet hours: 10 pm-8 am —No parties/ extra guests

Anjuna House - a Scandi riverfront forest getaway

Welcome to the enchanting retreat of "Anjuna," nestled among a sprawling forest in the heart of southern Indiana. This modern 4-bedroom, 3 bathroom luxury cabin features 14' floor-to-ceiling windows, and 1000+ sqft deck! Outside there are 12 acres of forest to explore, an outdoor shower and a tranquil river which meanders through the property. Anjuna is near Knobstone trail, Marengo Cave, and the bourbon trail in Louisville. Bring family, friends or just yourself to relax or explore at Anjuna!

Beachfront River Cottage

Escape to our Beachfront River Cottage for tranquility and breathtaking panoramic views of the Ohio River. Whether you're here for the Kentucky Derby, Music Festivals or a quiet weekend away, this charming retreat offers the rare luxury of a private beach w/fishing and modern comforts. Featuring a glass-enclosed, AC/Heated porch—perfect for morning coffee or sunset dinners year-round. Equipped with a full-size gas grill, Adirondack chairs, a picnic table, and a fire pit for cozy evenings.

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 180 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.

Enchanting Lakeside Cabin in 50 Acres of Gardens!

Escape to the Lakeside Cabin at Hollyhock Gardens, a secluded retreat where cozy cabin charm meets lake views. Nestled on 50 private acres, this lakeside cabin is ideal for romantic getaways, family vacations, or relaxing nature retreats. Enjoy wooded walking trails, open fields, and two covered porches overlooking the land. Inside, unwind with a hot soaking tub, in-unit laundry, and a fully equipped space. Just 21 miles from downtown Louisville, it’s a serene escape with easy access.

Iconic Lighthouse Estate on Scenic Ohio River!

Settle into this spacious 2,200-square-foot Prospect retreat along the Ohio River, accommodating up to 10 guests across a king suite, bunk room, and flexible loft. The home features 2.5 bathrooms, a full galley kitchen with dishwasher and Keurig, a bar family room, and a living room with a smart TV. A private in-home elevator connects the two levels — a rare touch that sets this retreat apart. Five dedicated parking spaces, whole-home Wi-Fi, and in-home laundry complete the package.

Charming Tiny House In Scottsburg

Welcome to your perfect little getaway in the heart of Scottsburg! This cozy, tiny house offers comfort, style, and convenience—just two blocks from the historic town square with local shops, cafés, and restaurants. Step outside and enjoy your own patio, or take a short walk to the square and explore all that downtown Scottsburg has to offer. Perfect for solo travelers, couples, or anyone looking to experience small-town charm from a cozy home base.

Basement apt. Country setting 2 bedrooms 1 bath

Quiet country setting in S. Indiana, only 20 minutes from Louisville Ky. Private entrance, two bedrooms and comfortable living room with a large tv. One bedroom has a queen bed and tv while the other has a queen bed and a bunk bed. Lucy our Aussiedoodle loves company and loves everyone. She’d love to get to know your dog also but 50lbs or less . You will need a leash as we do not have a fenced yard. We live upstairs if you need anything at all

Entire home: close to downtown Louisville, Ky!

Spacious, quiet home located just 15 minutes from downtown Louisville — perfect for traveling professionals, contractors, nurses, or extended stays. Enjoy reliable high-speed WiFi, a full kitchen, washer and dryer, comfortable bedrooms, and a safe neighborhood setting. Designed for longer stays, this home offers the space, convenience, and privacy hotels simply can’t match. Comfortable. Convenient. Stress-free.

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....