Vacation rentals in Charlestown

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Top-rated vacation rentals in Charlestown

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Guest favorite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 151 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.

Jun 26 – Jul 3

G$31,610 GYD per night

Guest favorite

Home in Jeffersonville

4.95 out of 5 average rating, 152 reviews

Cheerful 2 bedroom home, close to downtown

2 bedroom home & 1.5 bath. Fenced private courtyard. Walk to parks, dining & shopping in downtown Jeffersonville. Across the bridge from Louisville! Lots of light, chef's kitchen w kitchen wares and expandable dining table. 2 bedrooms (queen beds), and a comfy couch. Street parking w designated spot. We live on the street & use a security camera to confirm your arrival, departure, # of reserved guests. Non Smoking home. 8 min drive: Yum!Center/Convention Center/Bourbon distilleries/ restaurants

Sep 4 – 11

G$22,547 GYD per night

Guest favorite

Home in New Albany

5.0 out of 5 average rating, 297 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.

Oct 14 – 21

G$24,298 GYD per night

Guest favorite

Guest suite in Louisville

4.93 out of 5 average rating, 209 reviews

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Nov 5 – 12

G$15,682 GYD per night

Guest favorite

Guest suite in Borden

4.92 out of 5 average rating, 140 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.

Sep 12 – 19

G$23,861 GYD per night

Guest favorite

Cabin in Henryville

4.96 out of 5 average rating, 279 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.

Mar 11 – 18

G$77,212 GYD per night

Guest favorite

Home in Bedford

4.99 out of 5 average rating, 187 reviews

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 160 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.

Aug 18 – 25

G$28,934 GYD per night

Guest favorite

Home in Prospect

4.94 out of 5 average rating, 209 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.

Jan 16 – 23

G$58,463 GYD per night

Guest favorite

Guesthouse in Georgetown

4.92 out of 5 average rating, 189 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!

Jan 1 – 8

G$19,101 GYD per night

Guest favorite

Tiny home in La Grange

4.97 out of 5 average rating, 159 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

Nov 7 – 14

G$20,496 GYD per night

Guest favorite

Guesthouse in Jeffersonville

4.88 out of 5 average rating, 180 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.

Jul 16 – 23

G$22,244 GYD per night

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 169 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.

Jun 19 – 26

G$29,605 GYD per night