Holiday rentals in Charlestown
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Top-rated holiday rentals in Charlestown
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest suite in Jeffersonville
4.93 out of 5 average rating, 149 reviewsRIView 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.
10–17 Dec
Home in New Albany
5.0 out of 5 average rating, 293 reviewsWelcome 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.
5–12 Sep
Home in Jeffersonville
4.95 out of 5 average rating, 149 reviewsCheerful 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
8–15 Nov
Holiday rentals for every style
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Popular amenities for Charlestown holiday rentals
Other great holiday rentals in Charlestown
Home in Louisville
4.9 out of 5 average rating, 170 reviewsQuiet Neighborhood Home With Outstanding Location
27 Nov – 4 Dec
Home in Bedford
4.99 out of 5 average rating, 185 reviewsAtoka Farms
31 Jan – 7 Feb
Home in Hanover
4.93 out of 5 average rating, 113 reviewsCampus Cottage: Cozy, Convenient, Captivating
26 Jan – 2 Feb
Guest house in Louisville
4.91 out of 5 average rating, 447 reviewsCute Carriage House off Frankfort Avenue
17–24 Aug
Guest suite in Louisville
4.93 out of 5 average rating, 205 reviewsHide away close to everything
11–18 Aug
Flat in Charlestown
4.92 out of 5 average rating, 38 reviewsCozy hideaway on Yankee creek.
29 Jan – 5 Feb
Home in Charlestown
5.0 out of 5 average rating, 15 reviewsQuarry Eight
6–13 Sep
Home in Jeffersonville
5.0 out of 5 average rating, 33 reviewsBeachfront River Cottage
28 Nov – 5 Dec
Cottage in Jeffersonville
4.92 out of 5 average rating, 38 reviewsPeaceful Easy Feeling
30 Nov – 7 Dec
Barn in Sellersburg
4.97 out of 5 average rating, 38 reviewsWKU Man Cave (Efficiency Apartment)
1–8 Jan
Home in Prospect
4.94 out of 5 average rating, 16 reviewsNEW! Riverside Retreat w/ a VIEW
24–31 Aug
Cottage in Floyds Knobs
5.0 out of 5 average rating, 66 reviewsBright and Cheerful 1 Bedroom Cottage
21–28 Jan
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