Charles Town vacation rentals

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Discover a selection of 14 homes and other vacation rentals in Charles Town that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a fireplace and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Charles Town

Showing deals for:May 29 - Jun 5

Image gallery for Gruner Bungalow at Otium Cellars

Gruner Bungalow
9.8 out of 10, Exceptional, (103 reviews)
Exceptional
(103 reviews)

Gruner Bungalow at Otium Cellars

Purcellville

13% off
Price is $1,855
$12,982 for 7 nights
All fees included
Gruner Bungalow at Otium Cellars

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Find out more about Charles Town

Why visit Charles Town

  • Rich History: Explore Charles Town's historic sites and immerse yourself in its fascinating past, perfect for history enthusiasts.
  • Charming Town Square: Enjoy leisurely strolls in the picturesque town square, surrounded by beautiful properties that define Jefferson County.
  • Outdoor Adventures: Take advantage of urban parks and scenic countryside for family-friendly outdoor activities and relaxation.
  • Diverse Accommodations: Choose from cozy cabins, charming cottages, or modern apartments to suit any vacation style.
  • Friendly Atmosphere: Experience the welcoming vibe of Charles Town, making it an ideal destination for romantic getaways and family adventures.

Popular types of accommodation in Charles Town

Planning a getaway to Charles Town? Exciting choices await you. Discover the most sought-after vacation rentals, including houses, cozy cabins, and charming cottages. If you're considering a more urban experience, check out our selection of apartments and townhouse rentals, featuring modern amenities like beautiful wood floors. No matter your preference, Charles Town has the perfect accommodation for a memorable stay.

  • Houses: Ideal for families or groups, these homes offer spacious accommodations and a homey feel, making them the top choice for visitors to Charles Town.
  • Cabins: Perfect for those seeking a rustic experience, cabins provide a serene escape amidst nature's beauty, ranking second in popularity.
  • Cottages: These delightful, cozy retreats are great for couples or solo travelers looking for a charming getaway.
  • Apartments: Offering convenience and comfort, apartments are a popular option for those wanting easy access to local attractions.
  • Chalets: These stylish homes provide a unique lodging experience, combining comfort and character in the heart of nature.**

Top attractions near Charles Town

Charles Town, West Virginia, offers a delightful mix of romantic getaways and urban adventures. Visitors can explore urban parks, historic sites, and historic places that cater to those seeking cultural, outdoor, and family-friendly experiences. Whether you're looking for a scenic stroll or a rich dive into history, Charles Town has something for everyone to enjoy on their vacation.

  • Harpers Ferry National Historical Park: A captivating blend of history and culture, this park features picturesque landscapes, historic buildings, and engaging exhibits that tell the story of its significant role in American history.
  • Appalachian Trail Conservancy Headquarters: A hub for outdoor enthusiasts, this center offers information on the famous Appalachian Trail, along with family-friendly activities and adventure opportunities in the surrounding natural beauty.
  • Shenandoah Lake Beach: Enjoy a relaxing day at this scenic beach, perfect for swimming, sunbathing, and picnicking, surrounded by serene lake views and lush greenery.

Things to do recommended for couples

For a romantic getaway in Charles Town, indulge in luxury at Sleepy Hollow Country Club. Savor exquisite wines and entertainment at Breaux Vineyards, located 8 miles away. Unwind together with a relaxing treatment at Vivo Day Spa, just 6 miles from the heart of town.

Things to do recommended for families

Families visiting Charles Town can enjoy the serene nature at Clearbrook Park, engage in sports activities at Fireman's Field, and relax at Jim Barnett Park, all offering wonderful outdoor experiences just a short drive away.

Things to do recommended for groups

Experience the thrill of racing at Summit Point Motorsports Park, just 7 miles from Charles Town. Enjoy a round of golf at Locust Hill Golf Course for outdoor fun, or catch a performance at the charming Old Opera House, perfect for culture and family entertainment.

*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 Charles Town

When planning your trip—whether you're traveling with a group, your family, or pets, or if you're seeking extended stays—be sure to prioritize your preferences in your search. Here are some helpful Vrbo booking tips for you.

  • Traveling to Charles Town with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Charles Town with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Charles Town: For many families, a trip isn’t truly complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like feeding bowls and beds to ensure that your whole family feels at home.
  • Planning for a long term stay visiting Charles Town: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you'll be able to effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a fully-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Charles Town

Charles Town, West Virginia, offers a delightful blend of romance and adventure, perfect for city-themed vacations. Explore the charming town square and enjoy the beautiful properties that define Jefferson County. With its friendly atmosphere and rich history, visitors can immerse themselves in family-friendly excursions while soaking up the sunny weather. Nearby attractions provide a perfect backdrop to enjoy the scenic countryside, making Charles Town a must-visit destination for travelers seeking diverse experiences.

  • Harpers Ferry: Located 7 miles from Charles Town, Harpers Ferry is a charming city that offers visitors a perfect blend of outdoor adventure and stunning scenery. Nestled at the confluence of the Potomac and Shenandoah Rivers, it is a gateway to the Harpers Ferry National Historical Park. Here, you can explore hiking trails, take in breathtaking views from Jefferson Rock, or engage in recreational activities like kayaking and fishing. The area's rich history is palpable, with well-preserved landmarks and the chance to learn about its pivotal role in the Civil War.
  • Ranson: Just 0.4 miles from Charles Town, Ranson is an inviting city that promises a mix of outdoor activities and romantic experiences. Visitors will find a variety of attractions, including the local amusement park and shopping mall, making it a great spot for family fun or a leisurely day out. Ranson is also home to a racetrack and event venues, providing entertainment for sports enthusiasts. The nearby lake offers opportunities for relaxation and recreation, making Ranson a delightful addition to your travel itinerary.
  • Kabletown: Situated within the vicinity of Charles Town, Kabletown is a quaint village that captures the essence of outdoor beauty and romance. This serene locale is perfect for leisurely strolls through parks or picnics by the lake. The village offers ample opportunities for outdoor activities, including hiking and exploring the local recreational areas. For those interested in culture, a nearby museum provides insight into the area’s history, making Kabletown a peaceful retreat that complements your West Virginia adventure.

Best time to go to Charles Town

If you're planning a trip to Charles Town, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.6°F (-0.2°C)Light RainMostly SunnyAverageSlightly Low
February34.9°F (1.6°C)Light RainMostly SunnyAverageSlightly Low
March42.6°F (5.9°C)Light RainMostly SunnyAverageSlightly Low
April53.2°F (11.8°C)Light RainMostly SunnySlightly HighAverage
May63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
June71.4°F (21.9°C)Light RainMostly SunnyAverageAverage
July76.6°F (24.8°C)Light RainMostly SunnySlightly HighSlightly High
August74.5°F (23.6°C)Light RainMostly SunnyAverageAverage
September67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
October56.3°F (13.5°C)Light RainMostly SunnySlightly LowSlightly High
November44.1°F (6.7°C)Light RainMostly SunnySlightly LowSlightly High
December37.0°F (2.8°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you aiming to save money on your upcoming getaway? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect spot for your trip.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on the full booking amount. Being the planner definitely has its perks. 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 begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is your go-to place for planning new adventures, managing your itineraries, and keeping track of your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To start exploring Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The captivating area of Charles Town awaits your stay

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

Sightseeing in and around Charles Town

Do you want to find things to do in the city? Venture out of your cozy vacation rental and check out everything that Charles Town has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Sleepy Hollow Country Club (2.8 mi / 4.5 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)
  • 612 Vineyard (10.4 mi / 16.7 km)

Exploring the natural landscape of Charles Town

Whether you're an adventurous traveler or just want to take in the scenery, Charles Town is a great place to spend some time outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Shenandoah Lake Beach (6 mi / 9.6 km)
  • Chesapeake and Ohio Canal (9.6 mi / 15.4 km)
  • Mackintosh Fruit Farm (11.8 mi / 19 km)
  • Poor House Farm Park (15.2 mi / 24.5 km)
  • Crystal Grottoes Caverns (17.4 mi / 28.1 km)
  • Jim Barnett Park (17.6 mi / 28.3 km)

Traveling 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 center. If you can't find a flight that works for your travel itinerary, you might consider flying into 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, West Virginia, United States of America when booking a vacation rental?
When looking for the best area to stay in Charles Town, West Virginia, consider the charming downtown neighborhood, which offers a delightful mix of history and modern amenities. This area is not only picturesque but also conveniently located near several attractions. One of the highlights is the historic Charles Town Races and Slots, where you can enjoy live horse racing and gaming. Additionally, the nearby Civil War Battlefields provide a fascinating glimpse into the region's history, with opportunities for exploration and education.

Another great option is the surrounding areas that boast beautiful landscapes and outdoor activities. The proximity to the Appalachian Trail allows for hiking enthusiasts to indulge in breathtaking views and nature walks. In terms of vacation rentals, there are various properties available, ranging from cozy cottages to larger homes, suiting different group sizes and preferences.
How much does it cost to rent a vacation home in Charles Town?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Charles Town 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 Charles Town vacation house rentals?
You can find great discounts on house rentals in Charles Town 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 Charles Town?
In Charles Town, vacation houses are the most popular type of rental, with about 13 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for comfort and convenience. Additionally, there are several condos, apartments, and cottages, which offer a more compact living space while still providing essential amenities. For those seeking a rustic experience, several cabins are also available, often located near nature, providing a cozy retreat.
Are there any family house rentals in Charles Town?
In Charles Town, West Virginia, there are about 11 family-friendly rentals available, making it a great choice for families looking to explore the area. Many homes in this charming town offer spacious living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces superb for children to play. Visitors can find amenities such as Wi-Fi and air conditioning to enhance their stay.

The locale is rich in history, with nearby attractions like the historic Charles Town and the beautiful Civil War battlefield, providing opportunities for educational outings. Families can also enjoy local parks and outdoor activities in the surrounding natural landscapes.
Can I rent a vacation home with a pool or hot tub in Charles Town?
In Charles Town, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for relaxation and recreation. Travelers can find properties in various neighborhoods, offering easy access to local attractions and the beautiful West Virginia countryside. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas superb for entertaining or unwinding after a day of exploration. Inside, guests can expect amenities such as fully equipped kitchens, comfortable living spaces, and often multiple bedrooms, suiting families or groups.
Can I find long-stay vacation rentals in Charles Town?
A long-stay vacation rental in Charles Town 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 pet-friendly house rentals in Charles Town?
In Charles Town, there are several pet-friendly house rentals available, offering a welcoming environment for travelers with furry companions. Many of these properties come equipped with amenities such as spacious backyards, outdoor patios, and fully equipped kitchens, superb for families or groups looking to enjoy a comfortable stay. Some rentals may even feature additional conveniences like laundry facilities and ample parking.

The charming town is near various parks and outdoor spaces, providing great opportunities for walks and playtime with pets. The nearby Appalachian Trail offers scenic hiking options, and local parks like the Jefferson County Community Center Park provide open areas for pets to roam.
Are there any remote work vacation rentals in Charles Town?
In Charles Town, West Virginia, there are numerous options for remote work-friendly vacation rentals, with around 22 available throughout the area. These properties typically come equipped with essential amenities for working remotely, such as reliable Wi-Fi and dedicated workspaces. Many rentals also feature comfortable living areas, full kitchens for preparing meals, and sometimes outdoor spaces for a refreshing break during work hours.

The town itself offers a charming atmosphere, with nearby attractions like the historic Charles Town Races and the scenic Harpers Ferry National Historical Park, providing opportunities for relaxation and exploration after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Charles Town vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Charles Town 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 Charles Town?
In Charles Town, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals, making for a convenient stay. Many rentals also feature patios or decks, providing outdoor spaces to relax and enjoy the pleasant surroundings. Additionally, you'll often find coffee and tea makers for a cozy morning routine, as well as onsite parking for easy accessibility.
When is the best time to visit Charles Town for a vacation rental?
The peak season for visiting Charles Town is from February to April, a vibrant time that attracts travelers looking to enjoy the charming ambiance of this historic town. During these months, visitors can engage in various outdoor activities and explore the rich heritage of the area, including the picturesque scenery of the surrounding countryside.

April stands out as a particularly popular month, with comfortable temperatures ranging from the low 40s to mid-70s Fahrenheit. This delightful climate is great for leisurely strolls through the town's historic district, where you can admire well-preserved architecture and visit local shops. The early spring also heralds the blooming of flowers, enhancing the town's natural beauty and providing ample opportunities for memorable photographs.

For those who prefer a quieter experience and are looking for more budget-friendly options, November is a fantastic month to consider. While the peak tourist season has concluded, you can still relish the tranquil charm of Charles Town, with fewer crowds and the opportunity to enjoy the serene autumn landscape.
How early should I book a Charles Town vacation rental?
Book your Charles Town 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 Charles Town, West Virginia, United States of America?
In Charles Town, visitors can explore several attractions that highlight the area's rich history and natural beauty. The historic Charles Town area features charming 18th-century architecture, with sites like the Jefferson County Courthouse and the Old Opera House, which often hosts events and performances. Nearby, the Charles Town Race Track offers a lively option for horse racing enthusiasts and those looking for entertainment.

For outdoor activities, the beautiful Shenandoah River is great for kayaking, fishing, and hiking, with access points located near the town. The surrounding countryside is also home to several wineries and vineyards, providing scenic views and opportunities for tastings.
Can I change or cancel my Charles Town home rental booking on Vrbo?
To find Charles Town 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 Charles Town 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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