Best Vacation Homes in Charlestown
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
Hot Tub
Fireplace/Heating
Pool
Ocean View
US $697/Night
7 Nights - US $4,880
Apartment
9.2(5 Reviews)
1 Bedroom
1 Bath
3 Guests
301.39 ft²
- Fireplace/Heating
Balcony/Terrace
View
Pet Friendly
US $97/Night
7 Nights - US $679
House
9.4(10 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Kitchen
Parking
US $352/Night
7 Nights - US $2,461
House
9.8(52 Reviews)
2 Bedrooms
1 Bath
6 Guests
Oceanfront- Hot Tub
- Fireplace/Heating
- Ocean View
US $246/Night
7 Nights - US $1,720
House
7.5(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
1539.24 ft²
- Fireplace/Heating
Breakfast- Pet Friendly
- Parking
US $284/Night
7 Nights - US $1,991
House
9.0(24 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $303/Night
7 Nights - US $2,123
House
10.0(155 Reviews)
4 Bedrooms
3 Baths
10 Guests
3200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $557/Night
7 Nights - US $3,897
House
10.0(4 Reviews)
6 Bedrooms
5 Baths
14 Guests
8500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $3,032/Night
7 Nights - US $21,221
Charlestown Luxury Rentals
House
10.0(3 Reviews)
5 Bedrooms
4 Baths
10 Guests
5612 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $3,482/Night
7 Nights - US $24,375
House
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $545/Night
7 Nights - US $3,815
New
House
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $527/Night
7 Nights - US $3,691
House
9.2(26 Reviews)
3 Bedrooms
2 Baths
6 Guests
2600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $519/Night
7 Nights - US $3,635
House
9.6(25 Reviews)
3 Bedrooms
2 Baths
10 Guests
3149 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $499/Night
7 Nights - US $3,494
House
9.6(4 Reviews)
3 Bedrooms
3 Baths
10 Guests
2653 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $443/Night
7 Nights - US $3,098
House
3 Bedrooms
3 Baths
6 Guests
2604.87 ft²
Spa- Fireplace/Heating
- Parking
Internet
US $430/Night
7 Nights - US $3,010
Cabin
10.0(6 Reviews)
3 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
US $352/Night
7 Nights - US $2,463
Charlestown Pet Friendly Vacation Rentals
House
9.6(14 Reviews)
3 Bedrooms
1 Bath
6 Guests
990 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $116/Night
7 Nights - US $809
House
1 Bedroom
1 Bath
8 Guests
947.22 ft²
- Pet Friendly
- Parking
Child Friendly
Barbecue/Outdoor Cooking
US $243/Night
7 Nights - US $1,701
House
9.4(16 Reviews)
3 Bedrooms
1 Bath
8 Guests
960 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $266/Night
7 Nights - US $1,865
House
9.4(16 Reviews)
3 Bedrooms
1 Bath
8 Guests
960 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $235/Night
7 Nights - US $1,645
Hotel
8.5(565 Reviews)
7 Baths
344.45 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $88/Night
7 Nights - US $619
House
9.2(32 Reviews)
3 Bedrooms
1 Bath
5 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $131/Night
7 Nights - US $918
House
2.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $140/Night
7 Nights - US $980
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $150/Night
7 Nights - US $1,051
Charlestown Large Vacation Homes
House
9.6(21 Reviews)
5 Bedrooms
4 Baths
16 Guests
4871 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $740/Night
7 Nights - US $5,180
House
10.0(4 Reviews)
6 Bedrooms
3 Baths
8 Guests
2016 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $324/Night
7 Nights - US $2,271
House
4.5(32 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $255/Night
7 Nights - US $1,785
House
4.0(1 Review)
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $244/Night
7 Nights - US $1,708
House
3 Bedrooms
3 Baths
11 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $4,116/Night
7 Nights - US $28,815
House
5 Bedrooms
4 Baths
10 Guests
3500 ft²
- Kitchen
- Air Conditioner
- Child Friendly
Laundry
US $500/Night
7 Nights - US $3,500
New
House
5 Bedrooms
5 Baths
18 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $4,070/Night
7 Nights - US $28,488
House
4 Bedrooms
2 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,615/Night
7 Nights - US $11,305
Why Choose Rent By Owner for your Charlestown Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Charlestown
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination ensures you experience its local charm at its finest, making your stay in the region truly memorable and well-suited to your preferences.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the area experiences warm weather ideal for outdoor activities and sightseeing, making it perfect for exploring the region's scenic beauty and attractions.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Early Fall (September to October)
This period offers pleasant temperatures and fewer crowds, allowing you to enjoy the regional charm and outdoor pursuits at a more relaxed pace.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
The cold months bring cooler temperatures and quieter surroundings, providing a peaceful setting for those seeking a tranquil retreat in this destination.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Late Fall (November)
As the region transitions into winter, visitors will find fewer crowds and cozy conditions, ideal for discovering local culture and relaxing indoors.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Charlestown
How to Book Your Charlestown Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Charlestown
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a fully equipped patio or BBQ area, perfect for family gatherings or evening cookouts.
- Take advantage of spacious yards or gardens, ideal for relaxing, playing, or picnicking amidst the natural surroundings.
- Relax by a private or shared swimming pool, providing a refreshing escape during warm summer days here.
- Explore nearby trails or walkways suitable for hiking, biking, or leisurely strolls to experience the area's scenic beauty.
- Make use of private decks or balconies that offer picturesque views of the region’s landscape.
- Utilize outdoor fire pits or fireplaces for cozy evenings under the stars, perfect for bonding and storytelling.
- Access outdoor sports facilities such as tennis courts or volleyball areas, providing active recreation close to your rental.
Top Attractions Around Charlestown
What attractions are nearby?
Nearby, you'll find a variety of outdoor activities and local attractions that let you enjoy the natural beauty and charm of this destination.
Family Activities
- Charlestown State Park: Explore scenic trails, enjoy picnicking, and participate in outdoor activities amidst the natural beauty of this regional park.
- The Historic District: Discover charming local boutiques, dine at family-friendly restaurants, and learn about the area's rich history in this quaint district.
- Indian Creek Aquatic Center: Spend a fun-filled day swimming, sliding, and cooling off at the local aquatic center designed for family entertainment.
- Shelby County Fairgrounds: Experience seasonal events, fair rides, and cultural festivals that bring the community and visitors together here in the region.
Adult Activities
- Exploring the Charlestown State Park: Enjoy scenic hiking, birdwatching, and picnicking amidst natural beauty in this local outdoor oasis.
- Visiting the Historic Charlestown Courthouse Square: Experience the charm of downtown with boutique shops, restaurants, and historical architecture that highlight the area's rich heritage.
- Golfing at nearby courses: Tee off at acclaimed golf courses just outside the town to indulge in a relaxing day on the greens surrounded by picturesque scenery.
- Fishing and boating on the Ohio River: Spend your time engaging in water activities along the river, offering both serenity and adventure for those who love aquatic recreation.
Other Places to Stay in Charlestown, IN
Charlestown Township
Charlestown State Park
Charlestown Family Activities Park
Charlestown Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Arrival Early: Arriving early allows you to settle into your vacation rental and enjoy the peaceful surroundings of the area without rushing.
- Explore Local Events: Check out community happenings and seasonal events in the region to immerse yourself in local culture during your stay.
- Visit Nearby Outdoors Spots: Take advantage of nearby parks and natural attractions to experience the scenic beauty that makes this destination unique.
- Utilize Local Recommendations: Seek tips from your hosts or locals for hidden gems and must-see spots around here to enhance your trip experience.
Transportation Options
- Charlestown Amtrak Station: This station provides convenient rail travel options connecting you to major cities across the region.
- Local Bus Services: Regional bus services operate throughout the area, offering an affordable way to explore nearby attractions and destinations.
- Taxi and Rideshare Services: Taxis and rideshare apps like Uber and Lyft are readily available for quick, flexible transportation around here.
- Private Car Rentals: Several car rental agencies in the region offer vehicle options that give you the freedom to explore at your own pace.
Local Customs Options
- Southern Hospitality: Expect warm welcomes and friendly exchanges that reflect the area's tradition of Southern hospitality, making your stay in the region even more inviting.
- Participate in or observe regional festivals that celebrate the area's rich heritage and community spirit, offering an authentic cultural experience.
- Historic Preservation: Notice the community’s commitment to maintaining historic sites and architecture, which provides insight into the area's proud past and cultural identity.
- Coffee and Local Cuisine: Enjoy the custom of gathering over coffee or regional dishes at local eateries, fostering connections and immersing yourself in the area's culinary traditions.
Charlestown Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Charlestown?
There are a lot of options in Charlestown. If you plan on staying in the Charlestown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Charlestown:
- Riverfront retreat. Stunning view. Dock. 20 minutes to downtown Louisville.
- Beautiful 3-bedroom home close to Louisville!
- Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
- Historical and Spacious Shabby Cabin Retreat! Modern Amenities
- Spectacular Estate for the KY Derby 150 and PGA Championship
- Spacious Family Home for Louisville Trip of a Lifetime
- The Boathouse: A Peaceful Paradise
- The Riverside Retreat - Your Coastal Getaway
- Spacious 3 BR Ranch House W/Patio Yard in a quiet Suburb
- Riverfront Home w/Private Dock | Derby, Bourbon
2. Which vacation homes in Charlestown are best for families?
If you are looking for a family-friendly vacation home in Charlestown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Charlestown:
3. How many Rentbyowner vacation rentals are available in Charlestown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 68 in the Charlestown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Charlestown.
4. What is the cancellation policy for vacation rentals in this area?
The cancellation policy varies depending on the property owner. It is recommended that you review the specific listing's cancellation terms before booking, or contact the owner directly for clarification.
5. How do I confirm my reservation for a vacation rental in the region?
Reservation confirmation typically occurs after completing the booking process and receiving an email confirmation from the host. For detailed assistance, reaching out to the property owner can ensure your reservation is secured.
6. Are there any additional fees associated with booking a vacation rental here?
Additional fees such as cleaning, service charges, or security deposits may apply and are specified within each listing. Be sure to read the details carefully or contact the host if you have questions about extra costs.
7. What amenities can I expect at vacation rentals in this destination?
Amenities vary by property, but many rentals offer essentials like Wi-Fi, parking, and kitchen facilities. Check each listing for specific amenities to match your needs.
8. Is it possible to modify or extend my stay at a vacation rental in the region?
Modifications or extensions depend on the property's availability and the owner's policies. Contact the host directly through the booking platform to discuss potential changes to your reservation.
Charlestown Top Rated Vacation Rentals
Hotel
8.8(153 Reviews)
1 Bath
- Pool
- Breakfast
- Parking
- Air Conditioner
US $131/Night
7 Nights - US $918
Hotel
8.4(1001 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $82/Night
7 Nights - US $571
US $94/Night
7 Nights - US $661
Hotel
8.0(62 Reviews)
3 Baths
- Pool
- Parking
- Internet
- Child Friendly
US $146/Night
7 Nights - US $1,024
Hotel
7.7(167 Reviews)
7 Baths
279.86 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $83/Night
7 Nights - US $582
Hotel
6.6(274 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $101/Night
7 Nights - US $704
Hotel
4.9(45 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $80/Night
7 Nights - US $559
