Charles Town holiday homes

We found 540 holiday rentals — enter your dates for availability
Discover a selection of 14 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:25 Dec - 1 Jan

Welcome to your cooking retreat - Thermador Column Fridge and Freezer, Gas Stove, Huge Kitchen Sink, Coffee and Hot Coco Station and an Austrian Tile Stove
The deck features ~900 sq ft from the master bedroom to the kitchen and panoramic views of the vineyard and opposing ridge line. Comfortable seating for the whole group!
Pool features a connected hot-tub with waterfall into the pool BUT the best feature is the view
Newly replace 16' Windows give an expansive view of the house vineyard
Exceptional
(60 reviews)

Vinewood Estate Luxury Pool and Vineyard Retreat

Purcellville

8% off
NZ$26,678
for 7 nights, 1 chalet
NZ$3,811 per night
includes taxes & fees
Vinewood Estate Luxury Pool and Vineyard Retreat
Stream your favorite TV shows and movies with high-speed internet.
Warm up around the fire pit and enjoy the stunning mountain and pastoral views!
The Kitchen Nook offers additional seating, and a cozy place to read.
Gather and enjoy meals in the spacious, fully stocked kitchen.
Exceptional
(6 reviews)

The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm

Waterford

8% off
NZ$6,513
for 7 nights, 1 room
NZ$930 per night
includes taxes & fees
The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm
Dining
Living area
Private kitchen
Exterior
Exceptional
(30 reviews)

Spacious Loudoun Wine Country Retreat: Hot Tub, Mountain Views, Family-Friendly

Round Hill

20% off
NZ$13,887
for 7 nights, 1 home
NZ$1,984 per night
includes taxes & fees
Spacious Loudoun Wine Country Retreat: Hot Tub, Mountain Views, Family-Friendly
Separate entrance to the apartment, for those who booked for 16+ guests.
Downstairs Bar area with full kitchen
Harpers Ferry Vacation Rental - Front View
Gas Fireplace in Downstairs Seating Area
Exceptional
(116 reviews)

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry

6% off
NZ$8,793
for 7 nights, 1 home
NZ$1,256 per night
includes taxes & fees
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Exterior
Front Foyer
Sunroom with dining table
Exterior
Exceptional
(87 reviews)

Rural Home, Hot Tub, Campfire, Hardwood Floors

Harpers Ferry

6% off
NZ$4,175
for 7 nights, 1 home
NZ$596 per night
includes taxes & fees
Rural Home, Hot Tub, Campfire, Hardwood Floors
Terrace/patio
Pool
Dining
Exterior
Exceptional
(28 reviews)

Historic Booth House at the Harpers Ferry KOA

Harpers Ferry

26% off
NZ$7,404
for 7 nights, 1 home
NZ$1,058 per night
includes taxes & fees
Historic Booth House at the Harpers Ferry KOA
Living room/dining room from stairway landing. French doors to stone patio.
Farm sign with spring daffodils and weeping cherry in bloom at farm entrance
Outdoor dining
Interior
Exceptional
(113 reviews)

Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704

Leesburg

15% off
NZ$5,345
for 7 nights, 1 home
NZ$764 per night
includes taxes & fees
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704
Exterior
Open concept kitchen
Outdoor dining
Living room with wood stove
Exceptional
(5 reviews)

Sunset Lion Mountain Cabin near a Lake & Vineyards

Harpers Ferry

8% off
NZ$5,592
for 7 nights, 1 cabin
NZ$799 per night
includes taxes & fees
Sunset Lion Mountain Cabin near a Lake & Vineyards
Dining
Terrace/patio
Interior
Living area
Exceptional
(46 reviews)

Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues

Bluemont

8% off
NZ$6,193
for 7 nights, 1 home
NZ$885 per night
includes taxes & fees
Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues
Exterior
Living Room With Stone Fireplace, Big Screen TV, and Pull Out Sofa
Terrace/patio
Stone gas fireplace
Exceptional
(133 reviews)

Hot tub, Campfire ring and great location!

Harpers Ferry

6% off
NZ$4,175
for 7 nights, 1 home
NZ$596 per night
includes taxes & fees
Hot tub, Campfire ring and great location!
Living area
Fire pit
Exterior
Private kitchen
Exceptional
(9 reviews)

Escape from the City. House near Harpers Ferry

Knoxville

8% off
NZ$2,747
for 7 nights, 1 cottage
NZ$392 per night
includes taxes & fees
Escape from the City. House near Harpers Ferry
Interior
Dining
Interior
Exterior
Exceptional
(130 reviews)

Bavarian Style Country Home on 120 Acres of Fields and Forests

Hedgesville

8% off
NZ$3,355
for 7 nights, 1 home
NZ$479 per night
includes taxes & fees
Bavarian Style Country Home on 120 Acres of Fields and Forests
Back yard
Interior
Interior
Bedroom #3
Exceptional
(41 reviews)

A Place to Get Away From It All

Knoxville

8% off
NZ$3,172
for 7 nights, 1 home
NZ$453 per night
includes taxes & fees
A Place to Get Away From It All
Room
Exterior
Miscellaneous
Living area
Exceptional
(16 reviews)

Cozy Cottage. Great hikes nearby, & walking distance to historic Harpers Ferry..

Harpers Ferry

8% off
NZ$2,429
for 7 nights, 1 cottage
NZ$347 per night
includes taxes & fees
Cozy Cottage. Great hikes nearby, & walking distance to historic Harpers Ferry..
Interior
Exterior
Living area
Dining
Exceptional
(75 reviews)

Storybook cottage on Leesburg's most historic block — walk to everything

Leesburg

8% off
NZ$7,591
for 7 nights, 1 home
NZ$1,084 per night
includes taxes & fees
Storybook cottage on Leesburg's most historic block — walk to everything
Interior
Living area
Property grounds
Exterior
Exceptional
(8 reviews)

Upscale Harpers Ferry Getaway

Harpers Ferry

8% off
NZ$5,423
for 7 nights, 1 home
NZ$775 per night
includes taxes & fees
Upscale Harpers Ferry Getaway
The Front Foyer Leading Up to Upper Master Bedroom
Hot Spring Rhythm 7 person Hot Tub
Upstairs Master Bedroom with King Bed and reflection in mirrors
Large Kitchen with Cherry Cabinets and Sub Zero refrigerator
Exceptional
(20 reviews)

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Harpers Ferry

7% off
NZ$4,134
for 7 nights, 1 home
NZ$591 per night
includes taxes & fees
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Main sitting area
Springtime at The Cottage
Kitchen
Fire Pit
Exceptional
(119 reviews)

A Restored Wagon Barn On A 1790's Farm.

Purcellville

8% off
NZ$3,202
for 7 nights, 1 cottage
NZ$457 per night
includes taxes & fees
A Restored Wagon Barn On A 1790's Farm.
Room
Property grounds
Living area
Property grounds
Exceptional
(10 reviews)

Camp Nelson Wooded Mountainside Retreat

Lovettsville

11% off
NZ$3,516
for 7 nights, 1 apartment
NZ$502 per night
includes taxes & fees
Camp Nelson Wooded Mountainside Retreat
Interior
Room
Exterior
Outdoor dining
Exceptional
(36 reviews)

Mountain Farmhouse Suite Near Harpers Ferry

Knoxville

8% off
NZ$1,407
for 7 nights, 1 apartment
NZ$201 per night
includes taxes & fees
Mountain Farmhouse Suite Near Harpers Ferry
Exterior
Property grounds
Property grounds
Interior
Exceptional
(26 reviews)

Historic Mountain Cottage at Blue Ridge Overlook

Bluemont

8% off
NZ$6,351
for 7 nights, 1 home
NZ$907 per night
includes taxes & fees
Historic Mountain Cottage at Blue Ridge Overlook
Living area
Property grounds
My home from the road.
Private kitchen
Exceptional
(13 reviews)

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Bluemont

8% off
NZ$2,995
for 7 nights, 1 apartment
NZ$428 per night
includes taxes & fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Interior
Exterior
Room
Private kitchen
Exceptional
(15 reviews)

The Flag House

Harpers Ferry

12% off
NZ$3,862
for 7 nights, 1 home
NZ$552 per night
includes taxes & fees
The Flag House

  • 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 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)
  • Bluemont Vineyard (13.3 mi / 21.4 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)
  • 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)
  • Shenandoah River (29.6 mi / 47.7 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.*You must be at least 18 years old to participate in gambling activities in the United Kingdom. Please gamble responsibly. If you feel that gambling is affecting your life, seek help from organisations such as BeGambleAware at www.begambleaware.org or call their helpline at 0808 8020 133.
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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Charles Town holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Charles Town to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.