Charlestown holiday rentals

We found 310 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Charlestown that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Charlestown

Showing deals for:8 Jan - 15 Jan

Property grounds
Exterior
Living area
Interior
Exceptional
(87 reviews)

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Louisville

8% off
AU$9,915
for 7 nights, 1 home
AU$1,416 per night
includes taxes & fees
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Living room area 1 with queen bed and bunk beds
Exterior
Terrace/patio
Foyer as you walk in front door
Exceptional
(14 reviews)

Beautiful views and sunrises overlooking the water. Spacious home with elevator.

Jeffersonville

20% off
AU$5,542
for 7 nights, 1 home
AU$792 per night
includes taxes & fees
Beautiful views and sunrises overlooking the water. Spacious home with elevator.
Front of the house with ample parking...
To make it even more special for you, we have a 6 people private hottub with lovely views of the Ohio river!
Kentucky Kingdom and Hurricane Bay Water Park is a MUST-SEE for families! It has fun-filled rides and activities for ALL ages! Get ready for all the splashing good memories that will last your family a lifetime!
As you open the door, this is the view you will be walking into.
Exceptional
(29 reviews)

Newspaper Featured Luxe Riverfront w/ Fire Pit Hot Tub Cinema Sauna Pets Views

Jeffersonville

7% off
AU$7,201
for 7 nights, 1 home
AU$1,029 per night
includes taxes & fees
Newspaper Featured Luxe Riverfront w/ Fire Pit Hot Tub Cinema Sauna Pets Views
Exterior
Pool
Living area
Living area
Exceptional
(11 reviews)

Safe, scenic, and convenient. Bordering a State Park!

Louisville

13% off
AU$5,632
for 7 nights, 1 home
AU$805 per night
includes taxes & fees
Safe, scenic, and convenient. Bordering a State Park!
Interior
Exterior
Dining
Private kitchen
Exceptional
(6 reviews)

3-bedroom condo in Norton Commons

Prospect

8% off
AU$3,676
for 7 nights, 1 apartment
AU$525 per night
includes taxes & fees
3-bedroom condo in Norton Commons
Dining
Now that you saw the highlights, let's give you a detailed tour of this lovely estate...
Interior
Living area
Exceptional
(30 reviews)

8BR Water View w/ Hot Tub, Fire pit, Dome, BBQ, Mins to Downtown & Lux Amenities

Jeffersonville

14% off
AU$8,092
for 7 nights, 1 home
AU$1,156 per night
includes taxes & fees
8BR Water View w/ Hot Tub, Fire pit, Dome, BBQ, Mins to Downtown & Lux Amenities
Room
Private kitchen
Living area
Interior
Exceptional
(35 reviews)

❤️Stay at Peppermint Cottage - Norton Commons -Walk eat & shop- free breakfast

Prospect

16% off
AU$3,802
for 7 nights, 1 home
AU$543 per night
includes taxes & fees
❤️Stay at Peppermint Cottage - Norton Commons -Walk eat & shop- free breakfast
Outdoor casual decking area
Living room w/pullout bed
Bedroom #2
Kitchen sotcked
Exceptional
(29 reviews)

Louisville GEM, newly furnished, super clean, in a safe trendy area

Louisville

10% off
AU$1,615
for 7 nights, 1 apartment
AU$231 per night
includes taxes & fees
Louisville GEM, newly furnished, super clean, in a safe trendy area
Room
Dining
Private kitchen
Outdoor dining
Wonderful
(17 reviews)

River City Retreat

Jeffersonville

7% off
AU$2,702
for 7 nights, 1 home
AU$386 per night
includes taxes & fees
River City Retreat
Private kitchen
Property grounds
Living area
Living area
Exceptional
(26 reviews)

Big 4 Cottage

Jeffersonville

7% off
AU$2,285
for 7 nights, 1 home
AU$326 per night
includes taxes & fees
Big 4 Cottage
Living area
Living area
Private kitchen
Living area
Exceptional
(19 reviews)

Waterfront Apartment, 2nd floor unit

Jeffersonville

7% off
AU$2,151
for 7 nights, 1 apartment
AU$307 per night
includes taxes & fees
Waterfront Apartment, 2nd floor unit
Living area
Riverfront view
Private kitchen
Dining
Exceptional
(57 reviews)

Waterfront Apartment - Downstairs Unit

Jeffersonville

7% off
AU$2,026
for 7 nights, 1 apartment
AU$289 per night
includes taxes & fees
Waterfront Apartment - Downstairs Unit

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The friendly city of Charlestown awaits you

The riverfront, island views and wildlife display a scene truly unique to Charlestown. Travellers appreciate the hiking in this welcoming city. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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 visit in the city? Venture out of your holiday home and experience everything that makes Charlestown a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for adventure or just want to appreciate the scenery, Charlestown is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Cherokee Park (14.9 mi / 23.9 km)
  • Louisville Mega Cavern (17.5 mi / 28.2 km)

Travelling to and around Charlestown

The nearest airport is in Louisville International Airport (SDF), located 18.8 mi (30.3 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday rental accomodation in Charlestown?
In Charlestown, holiday houses and cabins are the most popular types of holiday rentals, with several options available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many holiday houses also come with outdoor spaces such as decks or patios, where guests can enjoy the pleasant surroundings after a day of exploring local attractions, including the nearby Charlestown State Park.
Are there any remote work holiday rentals in Charlestown?
In Charlestown, Indiana, there are several remote work-friendly holiday rentals available, providing a conducive environment for those needing to balance work and leisure. Many of these properties come equipped with essential amenities such as high-speed internet and Wi-Fi, ensuring uninterrupted connectivity. Additionally, some rentals feature dedicated workspaces with desks and comfortable chairs, making it easy to set up a temporary office while enjoying your stay.Charlestown is conveniently located near various points of interest, including the Charlestown State Park, where you can take breaks from work to explore scenic trails and natural beauty. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Charlestown?
In Charlestown, popular rental amenities include kitchens, which allow guests to prepare their own meals, and onsite parking for convenience. Many properties also feature coffee and tea makers, ensuring that travellers can enjoy a warm beverage at any time. Additionally, paper towels are often provided for ease of cleaning and convenience during stays. Many rentals also come with balconies, offering a pleasant outdoor space to relax and take in the surroundings.
When is the best time to visit Charlestown for a holiday rental?
April is the most popular month to visit Charlestown, Indiana, as it marks the vibrant peak season from March to May. During this time, visitors flock to the area to enjoy the blooming spring flowers and the pleasant weather, which typically ranges from around 5 to 20 degrees Celsius. This mild climate is superb for outdoor activities, such as exploring the scenic Charlestown State Park or wandering through the charming downtown area, where you can find delightful shops and eateries.As the spring season progresses, the atmosphere in Charlestown becomes increasingly lively, making it an excellent time for travellers. You'll find various events and activities that cater to diverse interests, ensuring that there's something for everyone to enjoy.If you're looking for a more cost-effective option, consider planning your visit in December. While this month falls outside the peak travel season, it offers a unique charm with festive decorations and a quieter ambiance. You can still enjoy the local attractions without the bustle of larger crowds, making it a delightful time for a relaxing getaway.Ultimately, your choice of when to visit Charlestown will depend on your preference for vibrant springtime activities or a peaceful winter experience.
What are the top attractions in Charlestown?
In Charlestown, Indiana, visitors can explore several great attractions that highlight the area's charm and history. The Charlestown State Park is a significant draw, featuring expansive hiking trails, scenic views, and opportunities for wildlife observation. This natural setting is great for outdoor enthusiasts looking to engage in activities like hiking, fishing, and picnicking.The historic downtown area offers a quaint atmosphere with local shops and eateries, providing a glimpse into the community's heritage. Nearby, the Ohio River provides a lovely backdrop for leisurely walks and boating activities. Additionally, the Charlestown Pirate's Cove, a family-friendly water park, is a popular spot during the warmer months, featuring water slides and pools for a fun day out.For those interested in history, the local museums, such as the Charlestown Museum, present exhibits that delve into the town's past and its connection to the surrounding region.
Are all fees included in the Charlestown holiday homes prices shown on Stayz?
Stayz 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.
Are there any Charlestown holiday homes with parking?
Stayz offers a wide selection of holiday homes in Charlestown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Charlestown holiday homes?
You can find great discounts on holiday homes in Charlestown on Stayz, 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.
Can I change or cancel my Charlestown holiday home booking on Stayz?
To find Charlestown holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Charlestown?
A long-stay holiday home in Charlestown is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Charlestown holiday home?
Book your Charlestown holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Charlestown?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Charlestown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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