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Vacation rentals in Charlestown

Vacation rentals in Charlestown

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Charlestown

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

  • Sleep Easy in Jeffersonville #2
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1.5 shared bathrooms
    Sleep Easy in Jeffersonville #2

    Sleep easy in this private bedroom in Jeffersonville. The queen bed is a 12 inch memory foam mattress for a comfortable night sleep. Off-street parking, key pad entry, and quiet neighborhood make us an ideal location for a simple get away, but we are close enough to all the action. We are located 20 minutes to Churchill Downs, 15 minutes to the Yum Center and downtown Louisville. Not to mention the local restaurants in Downtown Jeffersonville, shopping, and entertainment are just minutes away.

    What guests are saying:

    “This is the best BNB that we have found. It is close to all the excitement of Louisville, while having the small town benefits. Michelle is an awesome host, she makes sure all of your needs are taken care of while giving you privacy. They went above and beyond to help us during our stay. We would absolutely recommend them to anyone looking to stay in the area.”

  • Cute, Cozy Space in Southern Indiana
    SUPERHOSTEntire house · 3 guests · 1 bed · 1 bathroom
    Cute, Cozy Space in Southern Indiana

    Cute, cozy space in the heart of Jeffersonville, IN. Little League ball field just down the road if you'd like to check out a game. Also, close proximity to several restaurants in downtown Jeffersonville or just a short drive to downtown Louisville, where you can find lots of entertainment for both the daytime and the nighttime. NOTE: Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.

    What guests are saying:

    “In a non-pandemic world the location is unbeatable. You are extremely close to downtown Jeffersonville and all the activities it has to offer. It’s also just a short 10 minute ride across the bridge to downtown Louisville where you could enjoy 4th street live or take in a concert at the Yum Center. In a pandemic world the backyard was just what was needed to allow my weary traveling self some fresh air while adhering to social distancing.”

  • The Waverly - Modern Clifton carriage house
    SUPERHOSTEntire guest house · 2 guests · 1 bed · 1 bathroom
    The Waverly - Modern Clifton carriage house

    Filled with natural light and a variety of art, this brand new and ultra modern carriage house is walking distance to entertainment, coffee shops, restaurants, bars, and boutiques. The perfect place for business or pleasure travelers.

    What guests are saying:

    “Do not hesitate to stay here!!!!! This is without a doubt one of the nicest AirBNB that I have ever stayed in. Very very clean, great location, outstanding hosts and everything is as pictured. Parking is excellent. Hosts are very communicative and available should you need anything. The space is absolutely gorgeous and has everything you could need. It would also be great for longer stays, as it is laid out so nice and has everything you could need or want.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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  • Unique stays

Popular amenities for Charlestown holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Charlestown

HIghlands Modern Get Away
SUPERHOSTEntire guest house
HIghlands Modern Get Away
Price:€60 / night
The River House
SUPERHOSTEntire house
The River House
Price:€278 / night
Duplex Digs for Always Dreaming in Louisville
SUPERHOSTEntire flat
Duplex Digs for Always Dreaming in Louisville
Price:€60 / night
Designer Home
Private room
Designer Home
Price:€38 / night
Welcome to your home away from home!
SUPERHOSTPrivate room
Welcome to your home away from home!
Price:€40 / night
Lower Cannons
SUPERHOSTEntire guest suite
Lower Cannons
Price:€49 / night
East End (Plainview) Peaceful Pine Retreat
SUPERHOSTEntire apartment
East End (Plainview) Peaceful Pine Retreat
Price:€93 / night
Tiny camper in the heart of the Highlands.
SUPERHOSTCampervan/Motorhome
Tiny camper in the heart of the Highlands.
Price:€49 / night
Private room, private bathroom, on site parking
SUPERHOSTPrivate room
Private room, private bathroom, on site parking
Price:€40 / night
Cute and quirky single apartment in St. Matthews
SUPERHOSTEntire flat
Cute and quirky single apartment in St. Matthews
Price:€53 / night
Travelers quarters at Midlane Farm
SUPERHOSTPrivate room
Travelers quarters at Midlane Farm
Price:€66 / night
*Sunny Oasis close to Hotspots in Bourbon Country
SUPERHOSTEntire house
*Sunny Oasis close to Hotspots in Bourbon Country
Price:€57 / night
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