Vacation rentals in Charlestown

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Top-rated vacation rentals in Charlestown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

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.

Dec 10 – 17

$127 per night
Guest favorite

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.

Sep 5 – 12

$91 per night
Guest favorite

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

Nov 8 – 15

$88 per night

Popular amenities for Charlestown vacation rentals

Stay near Charlestown's top sights

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

Other great vacation rentals in Charlestown

Guest favorite

Home in Louisville

4.9 out of 5 average rating, 170 reviews

Quiet Neighborhood Home With Outstanding Location

Nov 27 – Dec 4

$91 per night
Guest favorite

Home in Bedford

4.99 out of 5 average rating, 185 reviews

Atoka Farms

Jan 31 – Feb 7

$119 per night
Guest favorite

Home in Hanover

4.93 out of 5 average rating, 113 reviews

Campus Cottage: Cozy, Convenient, Captivating

Jan 26 – Feb 2

$84 per night
Guest favorite

Guesthouse in Louisville

4.91 out of 5 average rating, 447 reviews

Cute Carriage House off Frankfort Avenue

Aug 17 – 24

$57 per night
Guest favorite

Guest suite in Louisville

4.93 out of 5 average rating, 205 reviews

Hide away close to everything

Aug 11 – 18

$67 per night
Guest favorite

Apartment in Charlestown

4.92 out of 5 average rating, 38 reviews

Cozy hideaway on Yankee creek.

Jan 29 – Feb 5

$94 per night
Guest favorite

Home in Charlestown

5.0 out of 5 average rating, 15 reviews

Quarry Eight

Sep 6 – 13

$270 per night
Guest favorite

Home in Jeffersonville

5.0 out of 5 average rating, 33 reviews

Beachfront River Cottage

Nov 28 – Dec 5

$134 per night
Guest favorite

Cottage in Jeffersonville

4.92 out of 5 average rating, 38 reviews

Peaceful Easy Feeling

Nov 30 – Dec 7

$100 per night
Guest favorite

Barn in Sellersburg

4.97 out of 5 average rating, 38 reviews

WKU Man Cave (Efficiency Apartment)

Jan 1 – 8

$82 per night
Guest favorite

Home in Prospect

4.94 out of 5 average rating, 16 reviews

NEW! Riverside Retreat w/ a VIEW

Aug 24 – 31

$161 per night
Guest favorite

Cottage in Floyds Knobs

5.0 out of 5 average rating, 66 reviews

Bright and Cheerful 1 Bedroom Cottage

Jan 21 – 28

$90 per night

Destinations to explore

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  5. Charlestown