
Vacation rentals in Charles Town
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Top-rated vacation rentals in Charles Town
Guests agree: these stays are highly rated for location, cleanliness, and more.

The Patent House
Built around 1760, our log cabin sits on our 3 acre farmette, in the countryside in view of the foothills that separate VA, WV & MD. It's fully renovated, with a master bedroom (queen) & full bath upstairs. There is a convertible sofa downstairs (full). Cabin is next door to our house & shares a fence with our pasture where our mini donkeys live. We have yappy dogs and friendly outdoor cats. We're in the country, so bugs make their appearance but they tend to go straight to the window sills.

Enchanting PET FREE W/Amazing ViewHot Tub Overlook
Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. Quiet away from the train in old town Large patio, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

❤️ Secluded 1940s Romantic Tiny House on the River
Relax and escape to the peace and quiet by the Potomac river, and wake to beautiful romantic views of the river and mountains, in this romantic 200 square foot tiny house situated on 2.5 acres, 450 feet of river front land. Explore and partake of all the activities on the river and surrounding area, just 1 mile from Shepherdstown. Fish, bike, kayak, tube, or just sit by the river and watch the birds and wild life. Read by the river or in the quiet comfort of the house, w/ some wine on us.

Luxury Mountain Getaway: Sunsets, Wines & Views.
Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Cozy West Virginia Treehouse
Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Cozy Pool & Hot Tub Retreat by Casino
Welcome to Charles Town, WV! This private pool house boasts two cozy bedrooms and two bathrooms. Perfectly blending relaxation and adventure, our space offers a refreshing outdoor oasis complete with a seasonal pool (available May-September), a premium Cal Spa hot tub open year-round, a convenient gas grill, a smokeless gas firepit, and a charming wood fire pit. Enjoy the many dining options, Hollywood Casino, outdoor adventures, and rich historical exploration right at your fingertips.

Creekside Retreat at the Jewel Vinsota
Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Gorgeous cabin on Blue Ridge
Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

Walnut Glen - Quaint 1 Bedroom Country Get-A-Way
Quaint and cozy studio apartment nestled on a quiet country lane just outside of Charles Town. Relax with a glass of wine on the private deck, enjoy a s'more at your personal fire pit or cool off in the built-in swimming pool. Keep an eye out for the deer that come to graze early morning and evening on the 3 acre property. Close to all area attractions without all the crowds. The loft apartment is in a separate building from our home, above my stained glass shop.

The Log Cabin
A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.

Kalia’s Mountain Momma Getaway
Find yourself in the peaceful woods of Shannondale for a relaxing getaway! Only 15-20 minutes from Historic Harper’s Ferry, breweries, wineries and hiking! If you must work while staying with us, (which would be most unfortunate) we have internet for your use! Book now or add us to your “Wishlist” for later. Send me a message to see what discounts are available!

Last Rodeo Cottage
Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.
Popular amenities for Charles Town vacation rentals
Other great vacation rentals in Charles Town

A Castle in the Woods at Bluemont VIrginia

Quiet Bedroom in a Charming Neighborhood

Little Big Sky! A cozy bedroom in the country!

Charming bed/bath w/views & space to telecommute

Apple B&B’s Pristine Suite

Room In Family Home – Near Harper’s Ferry & Casino

Boho Secluded Room

Historic Charles Town- Green room
Quick stats about vacation rentals in Charles Town
Total rentals
40 properties
Nightly prices starting at
R1,042 ZAR before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Charles Town?
Yes! Work meets play with ease at over 20 vacation rentals in Charles Town featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Charles Town have wifi?
Absolutely! We offer over 10 house rentals with wifi in Charles Town. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Charles Town?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Charles Town have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Charles Town. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Charles Town?
Charles Town has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Charles Town have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Charles Town. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charles Town have free parking?
Absolutely! We offer over 10 house rentals with free parking in Charles Town. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Charles Town?
Experience the best of Charles Town with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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