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.

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!

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.

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.

Close to Louisville~Hot Tub~Fire Pit~Game Room

Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full kitchen, laundry, and office. Guests will have full use of the grounds including the hot tub, fire pit, and the numerous covered decks & patios. Perfect romantic getaway or multi person retreat.

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 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.

Dee's Country Cabin

Historic hand hued log cabin with modern amenities. The large lawn is a park like setting that includes a charcoal grill, fire pit and picnic table perfect for cookouts and s'mores! Quiet getaway where guests can simply relax away from the city lights and noise. 15 minutes from Salem, 30 minutes from Paoli Peaks, 45 minutes from French Lick Casino or Louisville, Ky. Several parks within an hour or less drive that offer fishing, swimming, hiking, caves, biking, and canoeing.

The Writer’s Den

Take it easy at this unique and tranquil cabin getaway. Nestled on a wooded hillside overlooking the Louisville skyline, The Writer’s Den is a great place to call home. Located just off interstate 64 and 10 minutes from downtown Louisville, the cabin gives peaceful seclusion and location convenience for those looking to explore the area. With a screened in porch, back deck lounge, loft space and all the comfort amenities, you’ll be on your way to writing the next great novel!

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

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....