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Vacation rentals in Charlestown

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Top-rated vacation rentals in Charlestown

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Top guest favorite
An outdoor fire pit is surrounded by several wooden chairs, providing a gathering space for relaxation. The calm waters of the Ohio River reflect the night sky, with soft lights from boats creating a serene atmosphere. Low greenery and gentle clouds frame the scene.
Guest suite in Jeffersonville
4.95 out of 5 average rating, 230 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.

Guest favorite
A cozy outdoor firepit area is surrounded by Adirondack chairs, arranged in a circle on a gravel surface. Soft, warm lights hang overhead, illuminating the space against a serene, wooded backdrop, creating an inviting atmosphere for gatherings.
Villa in Prospect
4.92 out of 5 average rating, 119 reviews

Bourbon Trail, Firepit

After a beautiful drive along a tree-lined-canopied road, you will find Mint Julep Villa, located on a private 1.3 acre lot and just one street over from the Ohio River. Mint Julep Villa, is tastefully decorated for you and your family to enjoy your stay in the Louisville and Prospect KY area. No matter if it's the Bourbon trails, the Kentucky Derby, the numerous concerts and the many other attractions to draw you to Kentucky, Mint Julep Villa will be a place you'd be attracted to as well.

Top guest favorite
A charming two-story brick guest house is set against a lush green lawn. The exterior features large windows and a welcoming front porch with two white chairs. A gently curving driveway leads to the entrance, framed by manicured shrubs and a nearby tree.
Guesthouse in Prospect
5 out of 5 average rating, 101 reviews

Prospect Guest House

Take it easy at this unique and tranquil getaway. Newly remodeled, new bathroom and kitchenette. We live in the house next door, but guest house is private and very quiet. Nestled in horse country-neighboring horses graze in adjacent fields. Queen bed upstairs, converted sofa queen in loft. Air bed also available. Lots of closet space, extra large bathtub, internet and streaming TV. Great location whether you are touring the Bourbon Trail or attending any of the The Kentucky Derby events!

Top guest favorite
A single-family home is presented with a modern exterior featuring a combination of light grey siding and stone accents. Soft garden lighting illuminates the entryway steps, leading to a welcoming porch. Lush green lawn and trees frame the property, enhancing the inviting outdoor appeal.
Home in Jeffersonville
4.95 out of 5 average rating, 114 reviews

The Cloud - New Luxury Home With EV Charger

New 3 bed / 2 Bath, 2 King beds and 1 Queen. Spacious garage with EV charger, furnished patio with grill. Located in the heart of Jeffersonville's expansion and about 18 miles from Louisville International Airport and 7 Mi to Dtwn Louisville. Short distance to highways, shopping centers. Walking access to Vissing Park trails. Open floor plan with 10' ceiling, 65" smart TV and 50" smart TV in each bedroom. Kitchen fully equipped. Treadmill, 1 high chair and 1 portable pack and play for babies.

Top guest favorite
The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.
Cabin in Louisville
4.99 out of 5 average rating, 243 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favorite
The exterior of the estate features a charming porch adorned with potted plants and a flag. Sunlight filters through the surrounding trees, illuminating the stone and wood structure. A stone pathway leads through the lush green lawn, enhancing the inviting outdoor space.
Cabin in Henryville
4.97 out of 5 average rating, 348 reviews

Close to Louisville~Hot Tub~Fire Pit~Game Room

Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full kitchen, laundry, and office. Guests will have full use of the grounds including the hot tub, fire pit, and the numerous covered decks & patios. Perfect romantic getaway or multi person retreat.

Guest favorite
A modern kitchen area features stainless steel appliances, including a refrigerator and dishwasher, complemented by white cabinetry. A cozy living space is visible with a comfortable sofa and a coffee table, while natural light enters through a sliding glass door leading to a small balcony.
Apartment in Clarksville
4.92 out of 5 average rating, 195 reviews

Modern stay overlooking downtown

Forget your worries in this Luxury spacious and serene space. Make yourself at home! Relax in the unique 1Bedroom Queen size bed with Restaurants and smoothie bar in building! you’ll be close to Restaurants alongside the Ohio river, Kfc Yum Center, Downtown Walking bridge , Deserts , bars , music and more! Great wifi, meeting rooms open 24/7 charging stations for your electric vehicle! Last but not least Beautiful overlook of downtown Louisville on charming rooftop patio!

Top guest favorite
A patio area features several blue chairs positioned on a textured surface, with a stone bench visible nearby. Lush green trees surround the space, providing a natural backdrop. In the distance, a red structure can be seen, framed by the greenery.
Guest suite in Prospect
4.97 out of 5 average rating, 244 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

Superhost
A living area showcases a combination of modern and rustic elements. A leather sofa faces a brick wall with a decorative sign. A vibrant area rug adds color, while a blue armchair and a wooden coffee table provide seating and surface space. A breakfast bar is visible in the background.
Condo in Butchertown
4.88 out of 5 average rating, 108 reviews

Nulu/Butchertown 2 BR, along urban bourbon trail

Welcome to MARE on Washington, our Nulu/ Butchertown condo. We are located just steps away from the best food, drinks, and events in the derby city. We are located on a quiet street, only one block away from Main St. You can walk to breweries next door or even a soccer game at Lynn Family Stadium. The Yum Center is only a few blocks away, and we have one of the few properties located walking distance from Waterfront Park.

Top guest favorite
A cozy sitting area is furnished with two slender armchairs and a small ottoman, placed on a decorative rug. A flat-screen TV is mounted on the wall, and a narrow table holds decorative items. Sliding doors lead into the bedroom, enhancing the open feel.
Guesthouse in Germantown
4.97 out of 5 average rating, 801 reviews

Germantown Carriage House w/garage

Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. The carriage house has all the amenities for any length of stay, including garage parking with room for bikes. Only 2 miles from downtown Louisville, Germantown is nestled between the energetic and historic Highlands neighborhood, beautiful historic Old Louisville, and hipster NULU. Keyless entry makes for seamless check in and out.

Guest favorite
Home in Jeffersonville
4.92 out of 5 average rating, 157 reviews

Scandinavian Retreat: Charming Stay near Lou

Come stay in this cozy 3 bedroom, 1.5 bathroom townhouse, designed to make you feel at home while visiting Southern Indiana or Louisville, Kentucky. A few minutes to downtown night life, museums, Louisville, UofL, and close to bourbon trail this brand new home boasts new memory foam beds, furniture, full kitchen & more. Fast WiFi (~300mbs) 50" smart HDTV Parking for 2 cars 13 minutes to the YUM! Center

Top guest favorite
The exterior of a renovated farmhouse is surrounded by lush greenery. A spacious porch with seating is visible at the front, while a gravel path leads to the inviting entrance. The structure features a metal roof and warm-colored trim that complements the natural setting.
Farm stay in Goshen
4.98 out of 5 average rating, 350 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

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