Holiday rentals in Charlestown

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.

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!

Emerald Lake Retreat Charlestown

Water-View Sunroom | 4-Acre Property | Fire Pit From hosting afternoon picnics to making memories by the water, this vacation rental has everything you need for a blissful stay! Situated on a peaceful, spacious property, this 4-bedroom, 2.5-bath house boasts a fireplace, a charcoal grill, and a sunroom. Enjoy the peace and quiet around the crackle of the wood-burning fire pit and roast s’mores under the starry night sky. Whether you’re seeking serenity or lakefront fun, this gem has it all!

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.

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.

Watson Mansion Carriage House

Second floor of the Watson Mansion carriage house. Within walking distance of Charlestown venues, as well as the town square and Greenway Park. During the holidays, enjoy the lights and train rides. In warmer months, events are held in the square almost every weekend. Minutes to the Charlestown State Park. Conveniently located approximately 20 minutes from Louisville, so enjoy the safety of a small town without sacrificing big city amenities. Sleeps four with a queen sized murphy bed.

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

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.

Historic Shabby Cabin W/ Modern Comfort Sleeps 11!

Step back in time at our cozy 215-year-old historic cabin in Charlestown with modern comforts. This rustic retreat sleeps 11, perfect for family trips and group getaways. Relax around the outdoor fire pit, enjoy coffee on the front porch, and unwind on the back porch at sunset. The large open yard offers space to relax and play. Located just 6 miles from Charlestown State Park for hiking, nature, and scenic views ideal for a peaceful cabin escape.

Beach Vibes 2 mile to Whiskey Row Bourbon City

The beach vibes here are amazing 🤩! This special place is close to everything, making it easy to plan your visit. Only 2.7 mile away you will enjoy everything Downtown Louisville has to offer from a Bourbon Experience, great places to eat, bars, museums, arts, theater, music on Main Street also known to locals as Whiskey Row and Museum Row. Enjoy the local Indiana scene in Downtown Jeffersonville or Downtown New Albany with food and fun!

Riverfront Cottage

Wake up to peaceful Ohio River views at this charming 2-bed, 1 bath waterfront cottage, where mornings start with coffee on the screened porch and evenings end watching the sunset over the water. With private dock access, cozy indoor spaces, and a quiet setting just 25 minutes from downtown Louisville, this home is perfect for couples, small families, or anyone looking to unplug and relax by the river.