Vacation rentals in Charles Town

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Top-rated vacation rentals in Charles Town

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Top guest favorite
The log cabin features a welcoming front porch with seating and vibrant hanging plants. A gravel pathway leads to the cabin, surrounded by green grass and trees, while a fenced area is visible beside the porch, enhancing the private outdoor space.
Cabin in Charles Town
4.98 out of 5 average rating, 241 reviews

Vintage Riverfront Log Cabin “Emma” w/hot tub

“Emma” is a Shenandoah Riverfront Log Cabin hand built in 1900’ , she was just newly renovated. Come, Relax, you are on “River Time”. From the front porch, stroll the yard, and across the road, to access the Shenandoah riverfront dock. Here, the river is wide, and the view is amazing, launch a kayak or tube, fish from the dock. Enjoy your evenings around the campfire. From the cabin, you are just a few minutes away from Historic Harpers Ferry, wineries, breweries, hiking trails Enjoy!

Guest favorite
The kitchen area features a warm wood design with open shelving displaying plates and glasses. A stainless steel sink is accompanied by a dishwasher and a countertop appliance arrangement, including an air fryer and coffee maker. Soft lighting enhances the inviting layout.
Guesthouse in Lovettsville
4.92 out of 5 average rating, 215 reviews

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.

Guest favorite
A cozy tiny home is surrounded by lush greenery. Outdoor seating is provided with a small table and chairs, while planters filled with flowers enhance the space. A soaking tub is visible on the patio, adding to the charm of the outdoor area.
Tiny home in Harpers Ferry
4.96 out of 5 average rating, 156 reviews

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.

Top guest favorite
A living area features a comfortable beige sofa and an adjacent dining table with two chairs. A small desk with a chair and laptop is positioned nearby. Sunlight enters through a window adorned with white blinds, illuminating the relaxed atmosphere.
Home in Bolivar
4.97 out of 5 average rating, 306 reviews

Day Street - Walk to Harpers Ferry NP

This stylish apt with fenced yard is located just mins to the HFNP Park. 24/7 convenient store just 1 block away; library across the street; a corner lot in a very quiet neighborhood. Perfect place to start your hikes or just to rest for the weekend. The home has 1 BR, kitchen, full bath and coffee bar - Keurig; coffee pot; coffee press; pour over coffee; beans and grinder; teas bags w/ water pot and private parking for our guests. Please note that the living area for this home is upstairs.

Top guest favorite
The exterior of the home is showcased at dusk, highlighting its wooden façade and large windows. Warm outdoor lights create a welcoming atmosphere. A spacious deck with steps leads to the entrance, surrounded by wooded terrain, indicating a private and serene location.
Guest suite in Harpers Ferry
4.99 out of 5 average rating, 134 reviews

Tequila Sunset, Harpers Ferry. Entire first floor!

Welcome to Tequila Sunset in Harpers Ferry, WV! This beautiful, secluded home has stunning sunset views, you'll truly feel on top of the world! 100 mile vista of the gorgeous Blue Ridge Mountains. Entire first floor is yours, no shared spaces! Over 1200 SF of room to unplug & relax. King size Nectar bed, cozy indoor wood burning fireplace, outdoor firepit, 84" TV, & a private deck to enjoy the natural surroundings. Just 2 miles from the renowned Mountain Lake Club and the Appalachian Trail!

Guest favorite
A charming tiny house is set among greenery, featuring a red tin roof and welcoming porch. A new wooden staircase leads to the entrance, bordered by planters with colorful flowers. Surrounding foliage creates a serene, natural environment.
Tiny home in Jefferson County
4.89 out of 5 average rating, 489 reviews

❤️ 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.

Top guest favorite
A scenic outdoor view showcases a wooden deck winding down to a lush landscape. Vibrant flowers and greenery adorn the space, while a hot tub is visible nearby. A beautiful sunset casts warm hues across the sky, offering panoramic views of the valley below.
Guest suite in Harpers Ferry
5 out of 5 average rating, 268 reviews

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.

Top guest favorite
The treehouse is perched among tall trees, featuring a wooden deck that wraps around its structure. A gentle staircase leads to the entrance. In the foreground, purple flowers bloom beside a rock outcropping, enhancing the natural landscape under a bright blue sky.
Treehouse in Shepherdstown
4.97 out of 5 average rating, 374 reviews

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.

Top guest favorite
Guest suite in Summit Point
4.98 out of 5 average rating, 178 reviews

The Big Room - Historic Schoolhouse

Checkout as late as 8pm on Sundays! Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. The Railside Market serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia.

Top guest favorite
A restored log cabin features a red metal roof and wooden exterior, framed by trees and a grassy area. A dog lies comfortably on the ground in front of the porch, which is adorned with red chairs and a lantern.
Cabin in Shepherdstown
4.95 out of 5 average rating, 501 reviews

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.

Guest favorite
A rustic cottage features weathered wood siding and a welcoming front door. Two chairs sit on a circular brick patio, surrounded by colorful potted plants and neatly trimmed hedges. Lush greenery is visible in the background, enhancing the tranquil setting.
Cottage in Martinsburg
4.98 out of 5 average rating, 440 reviews

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.

Top guest favorite
A serene view of the Shenandoah Valley is presented, with a gradient of soft pink and purple hues in the sky during sundown. Lush greenery surrounds the area, enhancing the feeling of nature while a wooden deck is visible on the right side.
Guest suite in Bluemont
4.93 out of 5 average rating, 618 reviews

Blueridge Mountain Retreat Apartment

In the middle of VA wine country and only minutes from the Appalachian Trail, enjoy a private apartment in our mountain home with a separate entrance and your own deck with views of the Shenandoah Valley. There is a hot tub on the deck and a fire pit overlooking the valley. Plenty of wildlife. A welcome basket includes breakfast items.

Popular amenities for Charles Town vacation rentals

When is the best time to visit Charles Town?

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Avg. priceﺩ.ﺇ331ﺩ.ﺇ349ﺩ.ﺇ327ﺩ.ﺇ356ﺩ.ﺇ353ﺩ.ﺇ422ﺩ.ﺇ444ﺩ.ﺇ496ﺩ.ﺇ518ﺩ.ﺇ375ﺩ.ﺇ320ﺩ.ﺇ331
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Frequently Asked Questions

  • 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.

  • 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.

  • 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 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.

  • 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.

  • 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.

Quick stats about vacation rentals in Charles Town

  • Total vacation rentals

    Explore 40 vacation rentals in Charles Town

  • Nightly prices starting at

    Charles Town vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

  • Verified guest reviews

    Over 2,710 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Charles Town vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Charles Town rentals

  • 4.8 Average rating

    Charles Town stays are highly rated by guests—averaging 4.8 out of 5!