Charlestown vacation rentals

We found 288 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

Showing deals for:Jun 12 - Jun 19

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9.6 out of 10, Exceptional, (90 reviews)
Exceptional
(90 reviews)

Spectacular waterfront house!

Prospect

8% off
Price is $352
$2,465 for 7 nights
All fees included
Spectacular waterfront house!

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Find out more about Charlestown

Why visit Charlestown

  • Outdoor Adventures: Charlestown offers a variety of outdoor activities in state parks and beautiful lakes, perfect for adventure seekers.
  • Charming Town Square: The town square features local shops and eateries, creating a welcoming atmosphere for visitors.
  • Scenic Views: Enjoy captivating scenery and lush landscapes that enhance your outdoor living experience.
  • Diverse Accommodations: Choose from vacation homes, cozy apartments, and modern condos to suit your stay.
  • Friendly Community: Experience the warmth and hospitality of the locals, making your visit memorable.

Popular types of accommodation in Charlestown

Planning a getaway to Charlestown? Discover the perfect vacation rental for your stay. Choose from a variety of accommodations, including houses, cozy apartments, and modern condos. Whether you're looking for a spacious bedroom home, a comfortable unit at Parkside Trace Apartments, or a pet-friendly option, Charlestown has something for everyone. Enjoy the convenience and charm of this Southern Indiana destination while finding the ideal spot to relax and unwind.

  • Houses: The top choice for visitors, offering a spacious and comfortable setting ideal for families or groups.
  • Apartments: A popular option for those seeking a convenient stay, often located near local attractions.
  • Condos: A favored selection that combines the comforts of home with resort-style amenities.
  • Cabins: Perfect for a rustic getaway, these accommodations are nestled in nature for a peaceful retreat.
  • Cottages: A charming and cozy choice, great for couples or small families looking for a quaint experience.**

Top attractions in and around Charlestown

Charlestown, Indiana, offers a fantastic outdoor experience for adventure seekers and families alike. Visitors can explore a variety of attractions, including urban parks, state parks, and beautiful lakes. Whether you're looking to enjoy scenic views or engage in outdoor activities, Charlestown provides a perfect blend of nature and city life, making it an ideal destination for those seeking adventure and relaxation.

  • Charlestown State Park: Nestled just 3 miles from Charlestown, this state park offers breathtaking scenery and a wealth of outdoor adventures. Hike through lush trails, explore scenic vistas, and enjoy activities like fishing and camping amidst nature's beauty.
  • Louisville Waterfront Park: Located 13 miles away, this urban park is perfect for family outings. With sprawling green spaces, playgrounds, and stunning views of the Ohio River, it’s an ideal spot for picnics and leisurely strolls.
  • Woodford Farms Family Park: Situated within Charlestown, this eco-friendly park focuses on family fun, featuring playgrounds and open spaces for outdoor activities, making it a great place for kids to explore and play.

Things to do recommended for couples

Planning a romantic getaway in Charlestown? Be sure to visit Huber’s Orchard, Winery & Vineyards, located 14 miles away. Enjoy a cozy afternoon sampling wines amidst beautiful scenery, perfect for creating unforgettable memories together.

Things to do recommended for families

Your family vacation in Charlestown, Indiana, promises fun at the Charlestown Family Activities Park waterpark, relaxation at Deam Lake State Recreation Area just 10 miles away, and sweet treats at Schimpffs Confectionery, located 13 miles away. Enjoy memorable experiences together.

Things to do recommended for groups

Experience the scenic Covered Bridge Golf Club just 7 miles away, perfect for golf enthusiasts. Enjoy shopping and entertainment at Paddock Shops, located 11 miles from Charlestown. Finally, immerse yourself in culture and family fun at the Derby Dinner Playhouse, 13 miles away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip—whether it's with a group, family, pets, or for an extended stay—be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Charlestown with a group: Think about how many bedrooms you'll require, along with additional features like a full kitchen or outdoor area 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 a bit of a challenge. It’s important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions to enhance your experience.
  • Taking your pets with you to Charlestown: For many families, a vacation isn’t truly fulfilled without their furry companions. If you can relate to this, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels 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 perfect 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 near Charlestown

Charlestown, Indiana, offers a delightful blend of outdoor adventures and scenic views, perfect for families and friendly travelers alike. Explore the charming town square, where local shops and eateries create a welcoming atmosphere. Venture into nearby areas to discover coastal towns and lush landscapes that enhance your outdoor living experience. Whether you seek recreation or a touch of luxury, Charlestown promises an unforgettable getaway filled with friendly people and captivating scenery.

  • Sellersburg: Located 6 miles from Charlestown, Sellersburg is a vibrant city that offers a blend of business and family-friendly activities. Travelers often find themselves enjoying the local shopping mall center, which provides a variety of retail options and dining experiences. For outdoor enthusiasts, the recreational areas are ideal for leisurely strolls or family picnics. Noteworthy attractions include an event conference venue and a nearby racetrack, making it a perfect spot for both relaxation and entertainment.
  • Goshen: Situated 6 miles away from Charlestown, Goshen is known for its city vibe and outdoor experiences. Visitors are drawn to its shopping mall center and shopping areas, which cater to a diverse range of tastes. The scenic lake and river nearby offer beautiful views and opportunities for outdoor adventures, making it a great place for nature lovers. With its combination of business-friendly venues and recreational spaces, Goshen provides a well-rounded travel experience.
  • River Bluff: Just 7 miles from Charlestown, River Bluff is a charming neighborhood that emphasizes outdoor activities and stunning scenery. The area features campgrounds and shopping centers, catering to both adventure seekers and shoppers alike. Highlights include a beautiful lake, a national state park, and an archaeological site, which offer unique opportunities to explore nature and history. River Bluff is perfect for those looking to immerse themselves in the beauty of the outdoors while enjoying local amenities.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.7°F (0.4°C)Light RainMostly CloudyModerately LowSlightly Low
February36.1°F (2.3°C)Light RainMostly CloudyAverageSlightly Low
March45.9°F (7.7°C)Light RainMostly CloudyModerately HighAverage
April55.4°F (13.0°C)Light RainMostly SunnyModerately HighSlightly High
May65.5°F (18.6°C)Light RainMostly SunnyAverageSlightly High
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 HighSlightly High
October57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
November45.7°F (7.6°C)Light RainMostly SunnyModerately LowAverage
December38.7°F (3.7°C)Light RainMostly CloudyModerately LowSlightly Low

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. You might also discover that booking a longer stay can lead to significant savings. To help you find the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the organizer has its benefits. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides you with a convenient space to plan new trips, manage your current plans, and review your bookings. Your saved and booked properties are neatly organized into sections for Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • 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)
  • Riverfront Plaza Belvedere (14.3 mi / 23 km)
  • Cherokee Park (14.9 mi / 23.9 km)
  • Louisville Mega Cavern (17.5 mi / 28.2 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

What is the best area to stay in Charlestown, Indiana, United States of America when booking a vacation rental?
When considering a vacation rental in Charlestown, Indiana, the downtown area is an excellent choice. This vibrant neighborhood boasts a charming atmosphere, with easy access to local attractions and amenities. One of the highlights of staying in downtown Charlestown is the proximity to the scenic Charlestown State Park, which offers beautiful hiking trails and picnic areas, superb for nature enthusiasts. Additionally, the historic downtown area features delightful shops and eateries, allowing visitors to soak in the local culture.

Another appealing neighborhood is the area near the Ohio River. This picturesque location provides stunning water views and easy access to recreational activities like fishing and boating. Nearby, the Charlestown Marina serves as a great launching point for water activities and offers a lovely setting for a leisurely stroll along the riverfront.
How much does it cost to rent a vacation home in Charlestown?
Prices for vacation rentals in Charlestown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Charlestown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Charlestown vacation house rentals?
You can find great discounts on house rentals in Charlestown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Charlestown?
In Charlestown, vacation houses and cabins are the most popular types of rentals, with several options available throughout the area. These properties typically offer spacious rooms, often featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas great for families or groups. Many of these rentals are situated near local attractions such as the Charlestown State Park, which provides ample opportunities for outdoor activities like hiking and picnicking.
Can I find long-stay vacation rentals in Charlestown?
A long-stay vacation rental in Charlestown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Charlestown?
In Charlestown, Indiana, there are several vacation rentals available that cater to remote work needs. Travelers can expect properties equipped with essential amenities such as high-speed internet and Wi-Fi, ensuring a reliable connection for work purposes. Many rentals also feature dedicated workspaces, including desks and comfortable chairs, allowing for a productive work environment right within the accommodation.

Charlestown offers a charming small-town atmosphere, with local parks and recreational areas nearby, providing opportunities for relaxation after a workday. Additionally, the town's proximity to attractions like the Charlestown State Park enhances the appeal for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Charlestown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Charlestown with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Charlestown?
In Charlestown, popular vacation rental amenities include well-equipped kitchens, allowing guests to prepare meals during their stay. Many rentals also offer onsite parking, which is convenient for travelers with vehicles. Additionally, amenities such as coffee and tea makers are common, ensuring that guests can enjoy their morning beverages with ease. Rentals often provide paper towels for convenience and cleanliness, and many feature balconies where guests can relax and enjoy the fresh air.
When is the best time to visit Charlestown for a vacation rental?
April is the most popular time to visit Charlestown, Indiana, as it marks the peak season for travelers seeking a delightful getaway. From March through May, the area comes alive with blooming flowers and pleasant temperatures, making it an ideal time for outdoor activities. Visitors can enjoy scenic walks in the nearby Charlestown State Park, which features beautiful trails and opportunities for wildlife viewing, all while basking in the comfortable spring climate.

During April, temperatures typically range from the mid-40s to the low 70s Fahrenheit, providing a lovely backdrop for sightseeing and exploration. The vibrant setting is enhanced by local festivals and events that offer a chance to connect with the community and experience the charm of the area.

For those looking for a more budget-conscious option, consider planning your visit in December. While this month is generally quieter, it offers a unique opportunity to enjoy the holiday decorations and cozy winter charm of Charlestown. You can also find some great deals on vacation rentals, allowing you to experience the local culture without breaking the bank.

Ultimately, your choice of when to visit Charlestown will depend on whether you prefer the lively option of spring or the peacefulness of winter.
How early should I book a Charlestown vacation rental?
Book your Charlestown vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Charlestown, Indiana, United States of America?
In Charlestown, Indiana, visitors can enjoy various attractions that highlight the area's natural beauty and local history. Charlestown State Park offers expansive trails for hiking, biking, and horseback riding, along with picturesque views of the Ohio River. The park is a great spot for outdoor enthusiasts looking to explore nature.

The historic downtown area features charming shops and restaurants, where visitors can experience the local culture and cuisine. Additionally, the nearby Indiana State Museum showcases the region's history and heritage, providing insights into the area's past.

For families, the Charlestown Family Activities Park offers playgrounds and sports facilities, making it an excellent destination for a day of fun.
Can I change or cancel my Charlestown home rental booking on Vrbo?
To find Charlestown vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Charlestown vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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