Charlestown Holiday Houses

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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

Charlestown

Pam

includes taxes & fees

29 Nov - 30 Nov

A deck with a fire pit table and chairs, overlooking a body of water and forested area.

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

Prospect

Thomas c.

includes taxes & fees

8 Dec - 9 Dec

A wooden swing bed with a pergola roof, string lights, and a wooden deck.

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

Jeffersonville

Roberta

includes taxes & fees

1 Dec - 2 Dec

A backyard with a barbecue grill, outdoor seating, and a fire pit.

4. Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits

Irish Hill

peter m.

includes taxes & fees

30 Nov - 1 Dec

A living room with a glass coffee table, two armchairs, a sofa, a TV, and a bookshelf.

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

New Albany

Allan A.

includes taxes & fees

7 Dec - 8 Dec

A living room with a fireplace, leather armchairs, a coffee table, and a painting on the wall.

6. New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

South Louisville

Chayil B.

includes taxes & fees

18 Nov - 19 Nov

A living room with a sectional sofa, a fireplace, a flat-screen TV, and a zebra-patterned chair.

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

Clarksville

Jeff B.

includes taxes & fees

17 Nov - 18 Nov

A residential house with a garage, a driveway, and a tree in the front yard.

8. Tranquil 3-bedroom house Center of New Albany

New Albany

includes taxes & fees

15 Nov - 16 Nov

A two-story brick house with a front porch, a staircase, and a well-maintained garden.

9. Convenient & Cozy! Close to everything Louisville!

Belknap

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

10. Modern cabin very close to scenic riverfront walks

Hanover

MaKayla Q.

includes taxes & fees

12 Nov - 13 Nov

A neatly made bed with a green blanket, a pillow with a floral pattern, and a white pillow. There is a small wooden table beside the bed with a white basket underneath.

11. The Booker Noe Suite | Brick Home w/ Modern Design

Taylor Berry

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave. There is a dining area with a wooden table and a sofa. The walls are decorated with framed artwork.

12. Stable #5 ~ Mini Golf, Fire Pits, Games, Walkable

Irish Hill

Eric K.

includes taxes & fees

12 Nov - 13 Nov

A dining area with a long table set for six, surrounded by wooden chairs.

13. 10 Min to Louisville, Huge Hot Tub, Awesome Backyard

Clarksville

Madison H.

includes taxes & fees

7 Dec - 8 Dec

An outdoor seating area with a fire feature, a glass enclosure with a view, and a number '33' on the glass.

14. Dragons Perch | Hot Tub | 2 Bedroom

Taylor Berry

includes taxes & fees

30 Nov - 1 Dec

A modern kitchen with dark cabinetry, a central island, and pendant lighting.

15. Putt Putt House by Louisville Walking Bridge

Jeffersonville

Emily F.

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a central island, white cabinets, a brick accent wall, and a coffee sign.

16. Cozy NuLu Getaway | Private Yard + Free Parking

Phoenix Hill

Tracy H.

includes taxes & fees

19 Nov - 20 Nov

17. Dolphins Cove | Hot Tub | Near Churchill Downs 2 Bedroom

Taylor Berry

Jeremy P.

includes taxes & fees

18 Nov - 19 Nov

A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

18. 3-bedroom bungalow with , WiFi in Jeffersonville

Jeffersonville

Aimee H.

includes taxes & fees

12 Nov - 13 Nov

A transparent dome structure with a wooden deck, seating, and a television.

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

Prospect

Lisa R.

includes taxes & fees

22 Nov - 23 Nov

A dining area with a black table and chairs, a vase with dried plants, and wall-mounted wooden coasters with text.

20. Spacious family-friendly stay with arcade fun!

Wilder Park

Leah L.

View all properties

Learn more about Charlestown

Explore the historic Charlestown Square where local festivals showcase the town's community spirit throughout the year. Families flock to Charlestown Family Activities Park for its splash pad, playground, and picnic areas perfect for summer afternoons.

See all hotels in Charlestown

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

Top reviews in Charlestown

A bar area with multiple seating options and a large display of liquor bottles.

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Louisville

10/10 Excellent

Stephen

An outdoor seating area with wicker furniture and a fire pit.

Towneplace Suites By Marriott Louisville Downtown

Downtown Louisville

10/10 Excellent

Mark

A spacious indoor patio with a fire pit, wooden pergola, and comfortable seating areas.

Homewood Suites by Hilton Louisville Downtown, KY

Downtown Louisville

10/10 Excellent

Debra

A modern lobby with a central seating area, a reception desk, and a large screen.

Holiday Inn Express & Suites Louisville Downtown by IHG

Downtown Louisville

10/10 Excellent

Christopher

A hotel room with two beds, a TV, a desk, and a chair.

Comfort Inn & Suites Clarksville - Louisville North

Clarksville

10/10 Excellent

Great property. Huge room. It was super spacious. Two TVs. Bed was incredibly comfortable. Nice breakfast. Highlight was Joe on the front desk who covered quite a few roles. Incredibly friendly and great to chat with. Provided us with some great tips for our drive to Nashville. A genuine credit to the company. We're two weeks into a four week road trip and this was at the top end of properties in this price range. Thoroughly enjoyed our stay here.

Amanda

A modern interior with a fireplace, bookshelves, a green sofa, and leather chairs.

The Grady

Downtown Louisville

10/10 Excellent

I enjoyed my stay at the Grady. It’s such a beautiful boutique hotel and the staff are super friendly and helpful. Checking into the hotel was easy and the process was seamless. The rooms were spacious and very clean. The bed was comfortable and I had no issues with the heater in the room as I visited in the month February which was during winter. There is a restaurant downstairs and also nearby restaurants / cafes. I would highly recommend The Grady and I will definitely be returning...

Chloe

A spacious lobby with a high ceiling, a central chandelier, and seating areas with tables and chairs.

Omni Louisville Hotel

Downtown Louisville

10/10 Excellent

The Omni was absolutely incredible - super luxurious feel to everything and the library and speakeasy bars were amazing. The staff were really helpful and friendly. The fall city market has everything you could need. The only downside is that we had planned to spend the afternoon at the pool bar, however it was closed all afternoon and evening for a private event - it would have been nice to know when making our booking to avoid the disappointment when we got there. Otherwise, can’t really...

Lauren

Holiday Homes in Charlestown

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Charlestown holiday homes

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

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

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

4. Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits

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

6. New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

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

8. Tranquil 3-bedroom house Center of New Albany

9. Convenient & Cozy! Close to everything Louisville!

10. Modern cabin very close to scenic riverfront walks

11. The Booker Noe Suite | Brick Home w/ Modern Design

12. Stable #5 ~ Mini Golf, Fire Pits, Games, Walkable

13. 10 Min to Louisville, Huge Hot Tub, Awesome Backyard

14. Dragons Perch | Hot Tub | 2 Bedroom

15. Putt Putt House by Louisville Walking Bridge

16. Cozy NuLu Getaway | Private Yard + Free Parking

17. Dolphins Cove | Hot Tub | Near Churchill Downs 2 Bedroom

18. 3-bedroom bungalow with , WiFi in Jeffersonville

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

20. Spacious family-friendly stay with arcade fun!

Learn more about Charlestown

Top reviews in Charlestown

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

10/10 Excellent