Charles Town holiday rentals

We found 529 holiday rentals — enter your dates for availability
Discover a selection of 15 homes and other holiday rentals in Charles Town that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the amenities that you need and want, which might include parking and a pool. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Charles Town

Showing deals for:29 Jan - 5 Feb

Image gallery for Gruner Bungalow at Tranquility Farm & Winery

Sunroom
9.8 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)

Gruner Bungalow at Tranquility Farm & Winery

Purcellville

8% off
Price is AU$18,385
for 7 nights, 1 home
AU$2,626 per night
includes taxes & fees
Gruner Bungalow at Tranquility Farm & Winery

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    Enjoy full kitchens, laundry, pools, gardens and more

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The captivating area of Charles Town awaits your stay

Take a holiday to Charles Town and enjoy the area's entertainment, history and cathedral. Renowned for its horse riding, horse racing and casino gaming, this city welcomes all visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Charles Town

Are you hoping to find top things to see and do during your stay? Venture out of your holiday home and check out everything that makes Charles Town a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Locust Hill Golf Course (2.4 mi / 3.8 km)
  • Summit Point Motorsports Park (6.9 mi / 11 km)
  • 868 Estate Vineyards (7.5 mi / 12.1 km)
  • Breaux Vineyards (8.1 mi / 13.1 km)
  • Doukenie Winery (10 mi / 16 km)
  • Stoneleigh Golf and Country Club (12.1 mi / 19.4 km)

Exploring the natural landscape of Charles Town

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Charles Town is a great place to get outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Shenandoah Lake Beach (6 mi / 9.6 km)
  • Catoctin Valley (16.2 mi / 26.1 km)
  • Crystal Grottoes Caverns (17.4 mi / 28.1 km)
  • Jim Barnett Park (17.6 mi / 28.3 km)
  • Glenwood Park (20.4 mi / 32.8 km)
  • Oatlands Historic House and Gardens (21.4 mi / 34.5 km)

Travelling to and around Charles Town

Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), the closest airport, located 10.7 mi (17.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Hagerstown, MD (HGR-Hagerstown Regional), which is 29.5 mi (47.5 km) away.

Frequently asked questions

What is the best area to stay in Charles Town when booking a holiday rental?
When considering a holiday rental in Charles Town, West Virginia, the downtown area stands out as an excellent choice. This vibrant neighbourhood offers a charming blend of historic architecture and modern amenities, making it a delightful spot for visitors. The local dining scene is varied, with several restaurants that cater to a range of tastes, from casual eateries to more upscale options.

One of the top attractions in the area is the Hollywood Casino at Charles Town Races, which not only offers gaming but also hosts live horse racing events and entertainment options. Additionally, the nearby Charles Town Historic District is worth exploring, featuring beautifully preserved buildings and a rich history that can be felt as you stroll through the streets.

In terms of available properties, downtown Charles Town has a good selection of holiday rentals, ranging from cosy apartments to larger houses, accommodating various group sizes and preferences.

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What is the most popular type of holiday rental accomodation in Charles Town?
In Charles Town, holiday houses are the most popular type of holiday rental, with around 26 available throughout the area. These spacious homes are ideal for families or groups, often featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. Additionally, there are several condos, cottages, and apartments, which provide varied options for travellers seeking a more compact or unique stay. Cabins are also available for those looking to enjoy a rustic experience amid the beautiful West Virginia landscape.
Are there any family house rentals in Charles Town?
In Charles Town, West Virginia, there are numerous family-friendly house rentals available, with around 11 options to choose from. The area is known for its rich history and proximity to outdoor activities, making it an ideal spot for families. Many of these properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play. Additional amenities like Wi-Fi and air conditioning ensure a comfortable stay for all.

Visitors to Charles Town can explore nearby attractions such as the historic downtown area, local parks, and the scenic nature trails of the surrounding region. This locale also provides easy access to outdoor recreational opportunities, including hiking and fishing, superb for families looking to enjoy nature together.
Can I rent a holiday home with a pool or hot tub in Charles Town?
In Charles Town, West Virginia, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located in the picturesque Eastern Panhandle, offers a variety of rental options that cater to both relaxation and family fun. Many properties provide amenities such as private swimming pools, outdoor hot tubs, and spacious patios ideal for entertaining or unwinding after a day of exploring the area.

Travellers can also expect fully equipped kitchens, comfortable living spaces, and sometimes even outdoor cooking facilities like grills. The area's natural beauty and proximity to attractions such as the historic downtown and local vineyards make it a delightful choice for those seeking a holiday home with added leisure features.
Are there pet-friendly house rentals in Charles Town?
In Charles Town, West Virginia, there are several pet-friendly house rentals available, making it a great choice for travellers with furry companions. Many of these homes come equipped with amenities such as spacious backyards, modern kitchens, and comfortable living areas, ensuring a pleasant stay for both pets and their owners.

The area offers a charming blend of history and outdoor activities. Nearby, the picturesque Shenandoah River provides opportunities for kayaking and fishing, which can be enjoyable for pet owners looking to spend time outdoors. Additionally, the historic downtown area features pet-friendly cafes and shops, allowing you to explore the local charm while keeping your pet by your side.
Are there any remote work holiday rentals in Charles Town?
In Charles Town, West Virginia, there are numerous options for remote work holiday rentals, with around 44 properties available. This charming town offers a blend of historical significance and modern convenience, making it an attractive location for those looking to work while enjoying a getaway. Many rentals feature essential amenities such as high-speed internet and Wi-Fi, ensuring that you can stay connected during your stay.

Properties often come equipped with comfortable workspaces, allowing you to set up efficiently, as well as fully equipped kitchens for preparing meals. Travellers can expect a variety of accommodations, including cosy cottages and spacious homes, many of which have inviting living areas where you can unwind after a day of work.

Additionally, Charles Town boasts a number of local attractions, including historic sites and nearby outdoor activities, providing a great balance of productivity and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Charles Town?
In Charles Town, holiday rentals often feature a range of popular amenities that enhance guest comfort and convenience. Most properties come equipped with kitchens, allowing travellers to prepare their own meals. Additionally, many rentals include outdoor spaces such as patios or decks, great for enjoying the area's pleasant weather. For those who appreciate a good cup of coffee or tea, rentals typically offer coffee and tea-making facilities. Onsite parking is also a common feature, providing ease of access for guests arriving by car.
When is the best time to visit Charles Town for a holiday rental?
April is the most popular time to visit Charles Town, West Virginia, as the spring season brings a delightful atmosphere superb for exploration. From February through April, this region attracts visitors eager to enjoy the blooming scenery and participate in local events. During these months, outdoor activities flourish, with comfortable temperatures ranging from around 5 to 20 degrees Celsius, making it ideal for hiking and sightseeing.

In April, the area comes alive with festivals and activities, allowing guests to experience the vibrant culture of Charles Town. The nearby Harpers Ferry National Historical Park is particularly stunning this time of year, offering picturesque views and historical insights just a short drive away.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, where you can relish the beautiful autumn colours and enjoy the peaceful ambiance of the region, all while taking in the crisp fall air.
What are the top attractions in Charles Town?
In Charles Town, visitors can explore a variety of attractions that highlight the area's rich history and natural beauty. The historic downtown area features charming 19th-century architecture, with quaint shops and restaurants that offer a taste of local culture. A must-visit is the Jefferson County Courthouse, where significant events in American history unfolded, making it a fascinating spot for history enthusiasts.

For those interested in outdoor activities, the nearby Harpers Ferry National Historical Park is a short drive away and offers stunning views, hiking trails, and a glimpse into the region's role in the Civil War. It's a great place to explore the confluence of the Potomac and Shenandoah Rivers.

Additionally, the Charles Town Races and Slots is a popular attraction for those seeking entertainment, providing a lively option with horse racing and gaming options.
Are all fees included in the Charles Town 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 Charles Town holiday homes with parking?
Stayz offers a wide selection of holiday homes in Charles Town 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 Charles Town holiday homes?
You can find great discounts on holiday homes in Charles Town 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 Charles Town holiday home booking on Stayz?
To find Charles Town 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 Charles Town?
A long-stay holiday home in Charles Town 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 Charles Town holiday home?
Book your Charles Town 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 Charles Town?
Prices for holiday homes in Charles Town 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 Charles Town 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.