Photo by Mark Wilcoxson

Charlestown vacation rentals

We found 293 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Charlestown to find one that's 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:Oct 17 - Oct 24
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Find out more about Charlestown

Why visit Charlestown

  1. Outdoor Adventures: Enjoy a variety of activities such as hiking, picnicking, and exploring scenic parks and lakes.
  2. Family-Friendly Atmosphere: Charlestown offers a welcoming environment perfect for family vacations and solo travellers alike.
  3. Charming Neighbourhoods: Explore unique local neighbourhoods that feature recreational activities and luxury spots.
  4. Variety of Accommodations: Choose from private vacation homes, apartments, and condos to suit your travel needs.
  5. Natural Beauty: Experience the captivating scenery that combines both nature and urban life seamlessly.

Popular types of accommodation in Charlestown

If you're exploring the charming town of Charlestown, you'll find a variety of vacation rental options to suit your needs. Our most popular accommodations include houses, apartments, and condos. Whether you're searching for a cozy apartment in Charlestown or looking for the ideal Charlestown holiday rental, we provide the transparency and reassurance you need to secure your perfect getaway.

  • Houses: These are the top choice for visitors in Charlestown, offering spacious and comfortable stays for families or groups.
  • Apartments: A popular option for those seeking convenience and amenities, apartments provide a home-like atmosphere in the heart of the city.
  • Condos: Ideal for those wanting a blend of luxury and comfort, condos often feature modern designs and great locations.
  • Cabins: Perfect for a rustic getaway, cabins allow you to connect with nature while enjoying cozy accommodations.
  • Cottages: These charming retreats offer a quaint and peaceful escape, ideal for a relaxing vacation.**

Top attractions in Charlestown

Charlestown, Indiana, offers a fantastic blend of outdoor adventures and scenic beauty, making it an ideal vacation spot for travellers. With attractions such as urban parks, state parks, and serene lakes, visitors can enjoy a variety of experiences suited for families or solo adventurers. Whether you're hiking, picnicking, or simply soaking in the natural surroundings, Charlestown provides a delightful escape into nature and city life.

  1. Charlestown State Park: Located 4.8km away, this national park offers a stunning natural landscape filled with adventure opportunities, including hiking and camping. Experience the beauty of its scenic trails and outdoor vibes.
  2. Louisville Waterfront Park: Situated 14.8km from Charlestown, this urban park is perfect for families, featuring picnic areas, playgrounds, and beautiful views of the river, all while enjoying the lively city atmosphere.
  3. Mellwood Art Center: Also 14.8km away, this arts centre showcases local culture through art exhibits, studios, and events, providing a vibrant space for creativity and community engagement.

Things to do recommended for couples

For a romantic getaway in Charlestown, don't miss Huber’s Orchard, Winery & Vineyards, located 22.5km away. Enjoy a delightful day of wine tasting amidst beautiful scenery, perfect for couples seeking a charming and intimate atmosphere.

Things to do recommended for families

Your family will have a blast at Charlestown Family Activities Park, splashing in the waterpark. For a serene retreat, visit Deam Lake State Recreation Area, just 17.7km away, ideal for wellness. Don't miss Schimpffs Confectionery, 14.8km away, where sweet treats create delightful family moments.

Things to do recommended for groups

Groups visiting Charlestown can enjoy a round of golf at Covered Bridge Golf Club, experience the cultural charm of the Louisville Palace, and indulge in shopping and entertainment at Paddock Shops—all within a short drive of the town.

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

If you're travelling with a group, family, pets, or planning for an extended stay, it's important to prioritize your filters accordingly. 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 amenities like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these features and more on Vrbo.
  • Traveling to Charlestown with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you might want to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Charlestown: For many families, a trip isn't truly fulfilling without their furry companion by their side. If you can relate, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Charlestown: If you're in search of vacation rentals with special offers 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 features 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 adventure and scenic beauty, perfect for family-friendly vacations. Explore nearby cities and neighbourhoods that radiate a welcoming atmosphere, featuring luxury spots and recreational activities. Don't miss the charm of Charlestown, Massachusetts, and the vibrant energy of Boston. Whether you're seeking relaxation or adventure, this region promises a memorable experience infused with friendly locals and captivating scenery.

  • Sellersburg: Located a mere 9.7km from Charlestown, Sellersburg is a charming city that offers a blend of business, family-friendly activities, and outdoor experiences. Visitors can explore the local shopping mall and recreational areas, making it an ideal spot for a leisurely day out. The city is also home to notable landmarks such as a convention centre and a racetrack, providing ample opportunities for events and entertainment. Whether you're looking to shop, dine, or enjoy a family outing, Sellersburg has plenty to offer.
  • Goshen: Also situated 9.7km from Charlestown, Goshen is a vibrant city known for its outdoor spaces and community vibe. The city features a variety of shopping centres and recreational areas that cater to both locals and visitors. Nature enthusiasts will appreciate the nearby lake and river, perfect for a relaxing day by the water. Goshen’s mix of urban amenities and natural beauty makes it an engaging destination for business and leisure travellers alike.
  • Prospect: Located 12.9km away from Charlestown, Prospect is a welcoming city that caters to outdoor lovers and families. With a variety of shopping malls and recreational areas, this city provides a delightful experience for visitors. Local attractions include a beautiful lake and event conference venues, making it a great spot for both relaxation and events. Whether you're enjoying the scenic outdoors or attending a conference, Prospect is a fantastic destination to explore during your vacation.

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 LowModerately Low
February36.1°F (2.3°C)Light RainMostly CloudyAverageModerately Low
March45.9°F (7.7°C)Light RainMostly CloudyModerately HighAverage
April55.4°F (13.0°C)Light RainMostly SunnyModerately HighModerately High
May65.5°F (18.6°C)Light RainMostly SunnyAverageModerately 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 HighModerately 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 LowModerately Low

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We’re here to support you in finding the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous activities, and manage your travel arrangements. You’ll find your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.vrbo.com/en-ca/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:

  • 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 season are some things that can affect the price of a vacation home. Simply enter your travel dates to find your ideal match. From comfy cabins to expansive villas, all Vrbo vacation rentals provide amazing value.
How much does it cost to rent a beach house in Charlestown?
Prices for beach houses in Charlestown can vary depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use our filters to narrow your search by nearby activities, amenities, ratings and more.
What are the top attractions for families in Charlestown?
There are tons of fun things to see and do with the family in Charlestown, including:

  • Charlestown Family Activities Park
  • Charlestown State Park
  • Covered Bridge Golf Club

How old do you have to be to rent a vacation rental in Charlestown?
You'll need to check with the Charlestown vacation rental you're looking at on Vrbo as the minimum age differs. However, it's typically 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 depends on the property. Just enter your chosen travel dates to display a list of options offering extended stays. With loads of features such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get the perfect place to call your home away from home in Charlestown.

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