Holiday rentals in Charlestown

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Top-rated holiday rentals in Charlestown

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Guest favourite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 155 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Guest favourite

Home in New Albany

5.0 out of 5 average rating, 303 reviews

Welcome to the Bough House!

Listed on the National Registry of Historic Places, this beautifully renovated home offers vintage charm with modern amenities. Located just across the Ohio River from Louisville, only 6.6 miles from the Kentucky International Convention Center, 7 miles from the KFC YUM! Center, 12 miles from Churchill Downs, and one mile from shops and restaurants in historic downtown New Albany, IN, the Bough House is close to everything the Louisville region offers, with the peace of a quiet historic street.

Guest favourite

Guest suite in Borden

4.92 out of 5 average rating, 143 reviews

The White Rose of Starlight

The White Rose of Starlight is a one bedroom, one bathroom apartment with private access and is perfect for a weekend getaway or a week stay. We are just minutes away from popular Starlight destinations, Huber's Restaurant, Huber’s Winery, and The Woods ATV Adventures making it the perfect location for guests attending events or visiting for a weekend getaway. We are just 30 mins to Louisville and 15 mins to the interstate, making us easily accessible when visiting the Kentuckiana area.

Guest favourite

Cabin in Henryville

4.96 out of 5 average rating, 282 reviews

Stone Creek Cabin Retreat

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.

Guest favourite

Guest house in Hardinsburg

4.96 out of 5 average rating, 184 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Guest favourite

Home in Prospect

4.94 out of 5 average rating, 210 reviews

The River House

Welcome to a beautifully maintained home on the River. This home provides an open concept perfect for family or business gatherings. 4 private bedrooms with several spaces to add sleeping areas for additional guests. The elevator from the basement to the top floor provides easy access for our senior visitors and other guests. Three full baths will keep anyone from fighting over shower time and three levels of patios will provide your preferred view of the river. Welcome to relaxation.

Guest favourite

Guest house in Georgetown

4.92 out of 5 average rating, 190 reviews

Indian Creek Barn Cottage w/ EV & RV Charger

Private barn cottage in the knobs of Kentuckiana located on a 12 acre horse farm, recently renovated into a cozy comfortable space. The barn cottage is private space with 500 sqft, fully furnished 1 bedroom, 1 bath with living area, kitchenette equipped with a microwave, toaster, coffee maker, and mini refrigerator. Located just outside of New Albany, IN and less than 15 minutes to Louisville, KY allowing for the relaxation of the countryside, while also enjoying the city attractions!

Guest favourite

Tiny home in La Grange

4.98 out of 5 average rating, 163 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Guest favourite

Cabin in Salem

4.91 out of 5 average rating, 314 reviews

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.

Guest favourite

Guest suite in Clarksville

4.97 out of 5 average rating, 136 reviews

Cozy Getaway 1 Bedroom Suite in Clarksville

One bedroom suite with a private entrance. A spacious “his and her” closet and a washer and dryer. It has a sitting area with a comfortable futon/bed in one room and a queen bed and computer desk with free Wi-Fi. Also included is a kitchenette that has a mini refrigerator with a freezer, a microwave, an electric skillet, forks, spoons, knives, can opener and a Keurig coffee machine. Property has dedicated parking on one side and is next to a convenient store on the other side.

Guest favourite

Guest house in Jeffersonville

4.88 out of 5 average rating, 182 reviews

The Cottage Next Door

This charming open concept cottage has all the amenities including full kitchen, laundry, one bedroom with in suite full bath, patio, parking, fire pit, WiFi and so much more. You’ll love this place because of the ambiance, privacy, outdoor space, people and location. A lovely space to unwind and relax after a busy day whether it is work or play. We are a short 10/15 minutes drive to Louisville, Ky. Shared driveway, two parking spaces available. We do not allow pets.

Guest favourite

Guest suite in Prospect

4.97 out of 5 average rating, 175 reviews

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.