A forest path with a metal archway supported by concrete pillars.

Holiday Homes in Charlestown

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Charlestown holiday homes

A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

1. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (25 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is €147
includes taxes & fees
28 Sept - 29 Sept
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A spacious living room with a large sofa, a coffee table, and a TV. There is a balcony with a view of a lake.

2. The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!

The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
Prospect
9.8 out of 10, Exceptional, (10 reviews)
"My family and I had a wonderful trip. The house was absolutely beautiful. Everything was clean and well taken care of we couldn’t have asked for a better vacation"
United States
Thomas c.
The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!

3. Uptown Class

Uptown Class
New Albany
9.8 out of 10, Exceptional, (36 reviews)
"Communication was good,very responsive"
United States
Jerrel
The price is €380
includes taxes & fees
28 Sept - 29 Sept
Uptown Class
A living room with a glass coffee table, two armchairs, a sofa, a TV, and a bookshelf.

4. Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
New Albany
10.0 out of 10, Exceptional, (51 reviews)
"Nice property, we would stay again"
United States
Allan A.
The price is €182
includes taxes & fees
30 Sept - 1 Oct
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
A modern living room with a sofa, coffee table, TV, and wooden cabinet.

5. Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Jeffersonville
10.0 out of 10, Exceptional, (11 reviews)
"Has all the amenities you would need and is in a quiet neighborhood. Great for families."
United States
Stephen
The price is €228
includes taxes & fees
28 Sept - 29 Sept
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
A transparent dome structure with a wooden deck, seating, and a television.

6. LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property

LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property
Prospect
10.0 out of 10, Exceptional, (11 reviews)
"Absolutely love this property. We will stay everytime we come to Louisville. Can’t say enough about how great the home, area and host were"
United States
Lisa R.
The price is €372
includes taxes & fees
28 Sept - 29 Sept
LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property
A two-story house with a front porch, steps leading to the door, and a small garden area with plants and a pathway.

7. Blissful Bungalow on National Historic St in New Albany, 1 mile from Ohio River

Blissful Bungalow on National Historic St in New Albany, 1 mile from Ohio River
New Albany
9.8 out of 10, Exceptional, (18 reviews)
"Only about 15-20 minutes to Louisville KY. Had a great time!"
United States
Shari K.
The price is €277
includes taxes & fees
28 Sept - 29 Sept
Blissful Bungalow on National Historic St in New Albany, 1 mile from Ohio River
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

8. Country home with beautiful views and access to hiking, biking, and horse trails

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
9.8 out of 10, Exceptional, (43 reviews)
"Loved the dog-friendly house that even had a nice small fenced in area. Super quiet and close to the Knobstone trail for some exploring. The house was easy to find and access and the host was friendly. Thanks for the great place to stay!"
United States
Forrest K.
The price is €255
includes taxes & fees
28 Sept - 29 Sept
Country home with beautiful views and access to hiking, biking, and horse trails
A bedroom with a wooden bed, bedside tables, a nightstand, a window with blinds, and a wall-mounted lamp.

9. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
The price is €245
includes taxes & fees
28 Sept - 29 Sept
Convenient & Cozy! Close to everything Louisville!
A wooden sauna with benches, a window with a view, and a hanging basket.

10. +Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (96 reviews)
"Excellent location"
United States
Danielle S.
The price is €303
includes taxes & fees
6 Oct - 7 Oct
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
A two-story house with a front porch, a chimney, and a number '3935' on the door.

11. St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (13 reviews)
"cute housegreat location easy peasy"
United States
Lisa M.
The price is €291
includes taxes & fees
4 Oct - 5 Oct
St. Matthew’s - Walk to Shops & Restaurants
A two-story house with a porch, a front door, and a small front yard.

12. Stunning Victorian Home - prime location minutes from Louisville

Stunning Victorian Home - prime location minutes from Louisville
Jeffersonville
9.8 out of 10, Exceptional, (31 reviews)
"Clean"
United States
Jason M.
The price is €504
includes taxes & fees
5 Oct - 6 Oct
Stunning Victorian Home - prime location minutes from Louisville
A living room with a sectional sofa, a fireplace, a flat-screen TV, and a zebra-patterned chair.

13. Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row

Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
Clarksville
9.0 out of 10, Wonderful, (11 reviews)
"Was a great time and very clean "
United States
Jeff B.
The price is €194
includes taxes & fees
4 Oct - 5 Oct
Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
A backyard with a hot tub, patio furniture, and string lights.

14. King bed with backyard oasis

King bed with backyard oasis
New Albany
10.0 out of 10, Exceptional, (3 reviews)
"The property was nice and quiet and the back yard and home itself were beautiful."
United States
Hanna B.
The price is €255
includes taxes & fees
30 Sept - 1 Oct
King bed with backyard oasis
A green inflatable hot tub with handles, surrounded by a wooden fence and string lights.

15. Charming 1920’s shotgun in southern Indiana, minutes from downtown Louisville

Charming 1920’s shotgun in southern Indiana, minutes from downtown Louisville
New Albany
9.4 out of 10, Exceptional, (36 reviews)
"This was a wonderful rental for our multigenerational family visiting for college graduation. Highly recommend!"
United States
Aisha
The price is €196
includes taxes & fees
29 Sept - 30 Sept
Charming 1920’s shotgun in southern Indiana, minutes from downtown Louisville
A modern two-story house with a dark exterior, a covered front porch with stone pillars, and a stone pathway leading to the entrance.

16. The Adelyn, where comfort meets convenience

The Adelyn, where comfort meets convenience
Jeffersonville
10.0 out of 10, Exceptional, (9 reviews)
"The host was super responsive. The place was absolutely a gem!"
United States
Jeffery
The price is €271
includes taxes & fees
6 Oct - 7 Oct
The Adelyn, where comfort meets convenience
A wooden swing bed with a pergola roof, string lights, and a wooden deck.

17. King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
Jeffersonville
9.6 out of 10, Exceptional, (17 reviews)
"The property was very nice for our family getaway, would book again."
United States
Roberta
The price is €370
includes taxes & fees
28 Sept - 29 Sept
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
A hallway with a wooden desk, red chair, and artwork on the wall.

18. Chestnut Street Charmer-Walk to Louisville!

Chestnut Street Charmer-Walk to Louisville!
Jeffersonville
10.0 out of 10, Exceptional, (22 reviews)
"Great stay! We will be booking there for future trips to Louisville!"
United States
Brandon H.
The price is €295
includes taxes & fees
28 Sept - 29 Sept
Chestnut Street Charmer-Walk to Louisville!
A two-story residential building with a front porch, a wooden door, and a number '414' on the right side.

19. The Curated Chateau—Minutes from Louisville

The Curated Chateau—Minutes from Louisville
New Albany
9.8 out of 10, Exceptional, (47 reviews)
"It was a perfect stay for our weekend at Churchill Downs."
United States
Peggy S.
The price is €256
includes taxes & fees
28 Sept - 29 Sept
The Curated Chateau—Minutes from Louisville
A modern dining area with a round wooden table, leather chairs, and a chandelier.

20. ☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Jeffersonville
8.8 out of 10, Excellent, (43 reviews)
"Very good host. The bathrooms could use some work but otherwise good value. "
United States
John O.
The price is €348
includes taxes & fees
29 Sept - 30 Sept
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Charlestown Hotel Reviews

The Brown Hotel

The Brown Hotel

10/10 Excellent
"Great stay"
Meghan 1-night trip
Posted less than an hour ago
The Brown Hotel

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
428
Accommodation
805 Holiday Homes
Lowest Price
€147
Highest Price
€504