Vacation rentals in Charlestown

BRAND NEW, Jeff, IN Cottage, The Newport

Welcome home to this cozy family retreat. Enjoy this private 4 bedroom/2 bath home LESS than 10 minus to all the best things to do in Southern Indiana and Louisville! LESS than 15 mins to KY Expo Center and Churchill Downs. Less than 30 minutes to Huber's. Gather in the living room to play games, watch TV or cook in the fully equipped kitchen. Enjoy all of the local distilleries, or one of the many museums, catch a soccer or baseball game then grab a bite to eat in Jeffersonville or Louisville.

Location · Value · Quiet

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.

Family · Location · Nearby

The Riverside Retreat - Your Coastal Getaway

Take it easy at this unique and tranquil getaway, perfectly situated with the Ohio River right in your backyard. Relax on the spacious back deck and enjoy stunning river views while unwinding in a peaceful setting. This home has been recently updated with a refreshed kitchen, flooring, modern lighting, updated bedrooms, and a renovated shower, making it a comfortable and inviting retreat for the duration of your stay. The Riverside Retreat is the perfect place to recharge and enjoy the scenery

Location · Value · Heating

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.

Location · Family · Quiet

Cozy Neighborhood Home - 10 min to Louisville!

Relax just 10 minutes from downtown Louisville at this beautiful patio home in a newly built community. Perfect for a weekend trip, business travelers, those with pets, travel nurses, and others! Quick, easy access to River City via I-65 or East End Bridge from a quiet, charming neighborhood just blocks from the area’s newest restaurant corridor. We are dog friendly, and boast a large side-yard and sidewalks throughout. Also enjoy the neighborhood’s paved walking trail with a lake view.

Value · Family · Condition

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.

Value · Family · River

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.

Value · Location · Cleanliness

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.

Value · Family · Getting around

Historic Shabby Cabin W/ Modern Comfort Sleeps 11!

Step back in time at our cozy cabin dating back to 1815! This precious cabin in Charlestown has all of the 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.

Location · Value · Quiet

Riverfront Cottage | Dock + Kayaks Near Louisville

Escape to the Ohio River at this charming 2-bedroom waterfront cottage in Prospect, KY. Wake up to peaceful river views, enjoy coffee on the screened porch, relax in the patio seating, or catch a game on the outdoor TV. Take a kayak from the private dock, watch the sunset, and unwind by the water. With the entire cottage to yourself and Louisville just a short drive away, it’s the perfect blend of peaceful riverfront relaxation and easy access to the city.

Family · Location · Indoor spaces

Cozy Cottage on Famous Kentucky Farm

Curl up by a wood-burning fireplace in a charming 2-bedroom cottage on Foxhollow Farm - Kentucky's most beloved farm stay, featured on Bravo's Top Chef. Perfect holiday escape: 1,300 rolling acres, horse views from the porch, private nature trail, and Thanksgiving/Christmas/New Year's availability. Just 20 min from Louisville's holiday events, bourbon trail, and Churchill Downs. Book your winter retreat now, holiday weekends fill fast!

Location · Family · EV charging

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.

Family · Location · Check-in