Holiday rentals in Charlestown Township

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

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

Relaxing River Retreat with Private Pool

Beautiful river front vacation-like home with sparkling private pool and gorgeous landscaping for enjoying Oldham County's natural beauty. Pool has plenty of space to splash while enjoying the river view (pool is open from April through October, and is not heated). NOTE: This is NOT a party house. Parties are not allowed. Home is protected with ring cameras. Must be 25 years old to rent, per Oldham County regulations. Please also note home is on 3 levels and requires going up and down stairs.

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.

The Boathouse: A Peaceful Paradise

The Boathouse is located at the back of Tartan's Landing Marina off of the Ohio River. It sleeps up 7 people (1 king bed, 2 queen beds, 1 XL twin bed) has full kitchen and 2 full baths. Enjoy the infinity edge pool (open May-Oct), hot tub, outdoor fire pit, pickle ball area & private boat ramp (ARRANGEMENTS MUST BE MADE AHEAD OF TIME FOR A BOAT.) Heating the pool is optional for additional charge per day. All seasons are beautiful from the Boathouse located 30 min from downtown Louisville.

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.

The Lady Jinx Home - 3 BR/2.5 Bath - Entire Home

“The Lady Jinx” is a renovated 3 BR/2.5 Bath, Princess Anne-style Home built in 1895. This 2-story has tons of character from the detailed wood trim to the stain glass windows to the original interior doors to the gorgeous wood floors. The home is located in downtown La Grange, the only town in America that has an active train running along it’s Main Street, & is within walking distance to restaurants, shopping boutiques, museums, parks and entertainment with being only one block away!

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.

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.

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.

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!