Photo by Mark Wilcoxson

Charlestown vacation rentals

We found 276 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other vacation rentals in Charlestown that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the best amenities for spending time at your home away from home, including air conditioning and WiFi. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Charlestown

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Find out more about Charlestown

Why visit Charlestown

  1. Outdoor Adventures: Enjoy the scenic beauty of local parks and nature trails perfect for hiking and picnicking.
  2. Family-Friendly Activities: Discover various attractions that cater to families, ensuring fun for all ages.
  3. Cultural Exploration: Visit local museums and historical sites that showcase Charlestown's rich heritage.
  4. Charming Neighborhoods: Experience the welcoming small-town vibe and explore nearby friendly communities like New Albany.
  5. Diverse Accommodation Options: Choose from cozy apartments, stylish condos, and pet-friendly rentals for a comfortable stay.

Popular types of accommodation in Charlestown

Planning a getaway to Charlestown? You're in for a treat! This charming destination offers a variety of popular vacation rentals, including private homes, apartments, and condos. Whether you're searching for pet-friendly options, budget-friendly stays, or spacious townhouses, Charlestown has something to fit every traveler’s needs. Explore your ideal accommodation and get ready for a memorable trip!

  • Houses: The top choice for travelers in Charlestown, offering spacious accommodations perfect for families or groups.
  • Apartments: A popular option for those seeking comfort and convenience, ideal for solo travelers or couples.
  • Condos: These stylish units provide a blend of luxury and home-like amenities for a relaxing stay.
  • Cabins: A favored retreat for nature enthusiasts, offering a cozy escape in the woods.
  • Cottages: These quaint dwellings provide a charming atmosphere for a peaceful getaway.**

Top attractions in Charlestown

Charlestown, Indiana, offers a delightful mix of outdoor activities, scenic views, and family-friendly experiences. Visitors can explore urban parks, a sports museum, and various event and conference venues, making it an ideal destination for those seeking culture and adventure. Whether you're enjoying a day in nature or learning about local history, Charlestown has something for everyone to enjoy during their vacation.

  1. Kentucky International Convention Center: Located 15 miles from Charlestown, this venue is perfect for business travelers and hosts a variety of events, providing a professional atmosphere for networking and conferences.
  2. Charlestown State Park: Just 3 miles away, this park offers thrilling outdoor adventures, picturesque scenery, and a chance to connect with nature through hiking, biking, and wildlife watching.
  3. Louisville Slugger Museum: Situated 14 miles from Charlestown, this museum celebrates America’s beloved pastime, showcasing the history and craftsmanship of baseball bats while immersing visitors in sports culture.

Things to do recommended for couples

If you're seeking a romantic getaway in Charlestown, consider visiting Huber’s Orchard, Winery & Vineyards for a cozy tasting experience. For some live entertainment, head to Headliners Music Hall. If you prefer a luxurious day, play a round at Valhalla Golf Club, perfect for couples looking to relax together.

Things to do recommended for families

Your family will have a blast at Charlestown! Enjoy the excitement of the KFC Yum Center, have fun at the Charlestown Family Activities Park waterpark, and unwind at Deam Lake State Recreation Area, all offering fantastic experiences suitable for kids and parents alike!

Things to do recommended for groups

Explore the vibrant Mall St. Matthews for shopping and entertainment, catch a show at the historic Louisville Palace for a cultural experience, and enjoy a round of golf at Champions Pointe Golf Club for some outdoor fun, all within a short drive from Charlestown.

What do I need to keep in mind when booking a vacation in Charlestown

When planning your trip—whether you're traveling with friends, family, pets, or seeking extended stays—be sure to refine your search based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Charlestown with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Charlestown with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Charlestown: For many families, a trip isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Charlestown: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Charlestown

Charlestown, Indiana, offers a delightful blend of outdoor adventures and family-friendly activities. Explore the scenic beauty of local parks and nearby attractions like New Albany, where friendly neighborhoods welcome you. Enjoy the charm of small-town vibes while discovering unique spots such as the private castle nearby. Whether you're seeking budget-friendly excursions or a peaceful retreat, Charlestown and its surroundings promise a memorable vacation experience for everyone.

  • Louisville: Located 14 miles from Charlestown, Louisville is a vibrant city known for its rich cultural scene and outdoor experiences. As the largest city in Kentucky, it offers a plethora of activities, including shopping at bustling malls and attending live music concerts. Visitors can explore local landmarks such as the Kentucky International Convention Center and the iconic Churchill Downs, home of the famous Kentucky Derby. The city's atmosphere is perfect for families and business travelers alike, making it a well-rounded destination for a day trip or extended stay.
  • Sellersburg: Just 6 miles from Charlestown, Sellersburg is a charming small town that provides a mix of family-friendly activities and outdoor adventures. This community is ideal for those looking for a peaceful getaway with access to recreational areas and shopping centers. Sellersburg boasts attractions such as the local event conference venue, where various gatherings take place, and the nearby racetrack, which adds an element of excitement. Its close proximity to Charlestown makes it a convenient stop for travelers seeking a more laid-back atmosphere.
  • Goshen: Also situated 6 miles away, Goshen is a picturesque town that offers a delightful blend of outdoor activities and family experiences. Visitors can enjoy the beauty of nearby lakes and rivers, perfect for picnics or leisurely walks. The town features shopping malls and recreational areas, catering to both leisure and shopping enthusiasts. Its welcoming vibe and access to nature make Goshen an appealing choice for those looking to unwind and explore the great outdoors while still being close to Charlestown.

Best time to go to Charlestown

If you're planning a trip to Charlestown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January32.7°F (0.4°C)Light RainMostly CloudyModerately LowLow
February36.1°F (2.3°C)Light RainMostly CloudyAverageAverage
March45.9°F (7.7°C)Light RainMostly CloudyModerately HighAverage
April55.4°F (13.0°C)Light RainMostly SunnyModerately HighHigh
May65.5°F (18.6°C)Light RainMostly SunnyAverageHigh
June73.8°F (23.2°C)Light RainMostly SunnyAverageAverage
July77.0°F (25.0°C)Light RainMostly SunnyAverageAverage
August75.4°F (24.1°C)Light RainMostly SunnyAverageAverage
September69.6°F (20.9°C)Light RainMostly SunnyModerately HighHigh
October57.9°F (14.4°C)Light RainMostly SunnyAverageLow
November45.7°F (7.6°C)Light RainMostly SunnyModerately LowAverage
December38.7°F (3.7°C)Light RainMostly CloudyModerately LowLow

Booking with Vrbo is simple

Are you aiming to cut costs on your upcoming journey? Keeping your travel dates flexible can be a smart strategy, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash™ on the full booking amount. Being the organizer truly has its benefits! Become a member of our OneKey rewards program to enjoy exclusive savings and accumulate OneKeyCash™ on qualifying stays. Sign up now and begin reaping the rewards!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous ones, or manage your travel arrangements. You can view the properties you’ve saved or booked, organized into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

The friendly city of Charlestown awaits you

The riverfront, island views and wildlife display a scene truly unique to Charlestown. Travelers appreciate the hiking in this welcoming city. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Charlestown

Are you hoping to find attractions to see while you're in town? Venture out of your cozy vacation rental and experience everything that Charlestown has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Covered Bridge Golf Club (7 mi / 11.2 km)
  • Champions Pointe Golf Club (7.9 mi / 12.7 km)
  • Huber’s Orchard, Winery & Vineyards (14.1 mi / 22.7 km)
  • Louisville Zoo (17.2 mi / 27.7 km)
  • Churchill Downs (17.9 mi / 28.9 km)
  • Valhalla Golf Club (18.1 mi / 29.1 km)

Exploring the natural features in Charlestown

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Charlestown. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Deam Lake State Recreation Area (10.5 mi / 16.9 km)
  • Louisville Waterfront Park (13 mi / 21 km)
  • E.P. Tom Sawyer State Park (13.3 mi / 21.5 km)
  • Big Four Bridge (13.5 mi / 21.6 km)
  • Yew Dell Botanical Gardens (13.8 mi / 22.3 km)
  • Riverfront Plaza Belvedere (14.3 mi / 23 km)

Traveling to and around Charlestown

The nearest airport is in Louisville, KY (LOU-Bowman Field), located 15.9 mi (25.6 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Louisville Intl. Airport (SDF), which is 18.8 mi (30.3 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in Charlestown?
Length of stay, property type and time of year are some of the conditions that can influence the price of a vacation home. Simply enter your travel dates to find your ideal match. From cozy chalets to sprawling villas, all Vrbo vacation rentals offer incredible value.
How much does it cost to rent a beach house in Charlestown?
Prices for beach houses in Charlestown will vary depending on the size and style of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and the number of guests to view your vacation rental options and prices. From there you can use the filters to narrow down your search by ratings, nearby activities, amenities and more.
What are popular rental amenities in Charlestown?
A barbecue grill and an oven are two of the most popular rental amenities guests are searching for in Charlestown. Vrbo vacation properties come in many shapes, styles and sizes and include a range of features to make your trip relaxing and comfortable.
What are the top attractions for families in Charlestown?
If you're craving some entertainment for the family close to the center of Charlestown, check out Charlestown Family Activities Park.
How old do you have to be to rent a vacation rental in Charlestown?
You'll have to check with the Charlestown vacation home you'd like on Vrbo as the minimum age varies. However, it's normally 16, 18 or 21.
How long can I rent a vacation rental in Charlestown for?
The length of time you can book a vacation rental in Charlestown is up to the property. Simply enter your chosen dates to display a list of options offering extended stays. With plenty of creature comforts such as kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere perfect to call your home away from home in Charlestown.
Does Vrbo offer discounts for vacation homes in Charlestown?
On Vrbo, you'll find fantastic discounts and deals for Charlestown. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're planning a mini getaway or an extended stay, Vrbo offers a variety of options for all budgets and styles.

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