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 favourite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 149 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.

10–17 Dec

€ 161 per night
Guest favourite

Home in New Albany

5.0 out of 5 average rating, 293 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.

5–12 Sep

€ 119 per night
Guest favourite

Home in Jeffersonville

4.95 out of 5 average rating, 149 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

8–15 Nov

€ 118 per night

Popular amenities for Charlestown holiday rentals

Stay near Charlestown's top sights

Jayc Plus3 locals recommend
Copper Kettle10 locals recommend
Charlestown Pizza Company4 locals recommend

Other great holiday rentals in Charlestown

Guest favourite

Home in Louisville

4.9 out of 5 average rating, 170 reviews

Quiet Neighborhood Home With Outstanding Location

27 Nov – 4 Dec

€ 119 per night
Guest favourite

Home in Bedford

4.99 out of 5 average rating, 185 reviews

Atoka Farms

31 Jan – 7 Feb

€ 153 per night
Guest favourite

Home in Hanover

4.93 out of 5 average rating, 113 reviews

Campus Cottage: Cozy, Convenient, Captivating

26 Jan – 2 Feb

€ 107 per night
Guest favourite

Guest house in Louisville

4.91 out of 5 average rating, 447 reviews

Cute Carriage House off Frankfort Avenue

17–24 Aug

€ 77 per night
Guest favourite

Guest suite in Louisville

4.93 out of 5 average rating, 205 reviews

Hide away close to everything

11–18 Aug

€ 90 per night
Guest favourite

Flat in Charlestown

4.92 out of 5 average rating, 38 reviews

Cozy hideaway on Yankee creek.

29 Jan – 5 Feb

€ 121 per night
Guest favourite

Home in Charlestown

5.0 out of 5 average rating, 15 reviews

Quarry Eight

6–13 Sep

€ 357 per night
Guest favourite

Home in Jeffersonville

5.0 out of 5 average rating, 33 reviews

Beachfront River Cottage

28 Nov – 5 Dec

€ 167 per night
Guest favourite

Cottage in Jeffersonville

4.92 out of 5 average rating, 38 reviews

Peaceful Easy Feeling

30 Nov – 7 Dec

€ 131 per night
Guest favourite

Barn in Sellersburg

4.97 out of 5 average rating, 38 reviews

WKU Man Cave (Efficiency Apartment)

1–8 Jan

€ 98 per night
Guest favourite

Home in Prospect

4.94 out of 5 average rating, 16 reviews

NEW! Riverside Retreat w/ a VIEW

24–31 Aug

€ 194 per night
Guest favourite

Cottage in Floyds Knobs

5.0 out of 5 average rating, 66 reviews

Bright and Cheerful 1 Bedroom Cottage

21–28 Jan

€ 108 per night

Destinations to explore

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