Holiday rentals in Charles Town

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Top-rated holiday rentals in Charles Town

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cabin in Charles Town
4.98 out of 5 average rating, 248 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!

Top guest favourite
Home in Harpers Ferry
4.94 out of 5 average rating, 159 reviews

Spectacular View, PET FREE, Skylight and Hot Tub

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 peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, "Mind Blowing" 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

Top guest favourite
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, 277 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.

Superhost
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
4.88 out of 5 average rating, 498 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 3 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.

Superhost
Holiday home in Charles Town
4.91 out of 5 average rating, 116 reviews

Mountain Ferry Landing - Riverfront Access

A perfect fun and relaxing getaway with friends and family. Come relax and enjoy the Shenandoah River at this brand new stylish home. Managed by Heaven On Earth, Mountain Ferry Landing is family owned and operated. The family has lived on this land for over 3 decades and wishes to provide travelers with a comfortable place with river access to enjoy the natural beauties of the Shenandoah. Whether you are coming for summer activities or a peaceful winter retreat, this place is for you!

Superhost
Home in Charles Town
4.89 out of 5 average rating, 136 reviews

Historic Charles Town- Artist's Home

In historic downtown Charles Town, this relaxing home is a perfect get away and also close to many local attractions. Walk to restaurants, coffee shops, and boutiques. In a quiet neighborhood, 5 blocks from the charming downtown, this welcoming older house has historic details, charming artsy decor, covered front porch, covered back porch, and large fenced yard. One of the 4 bedrooms is on the 1st floor. 8 mins to historic Harpers Ferry, 12 mins to Shepherdstown shops and theater.

Top guest favourite
The cottage exterior features a combination of beige siding and stone facade, highlighting a spacious screened-in porch. A wooden deck extends from the front, offering access to the inviting outdoor space surrounded by grassy areas and shrubs.
Cottage in Shenandoah Junction
4.96 out of 5 average rating, 214 reviews

Modern, private cottage at Fairview Organic Farm

Discounts for stays of 5 nights or more. Sitting atop a hill on 23 acres at historic Fairview Organic Farm, Circa 1737, the newish cottage is surrounded by pasture, organic gardens, history & overlooks the Harpers Ferry Gap. We are just a few miles from Charles Town, Harpers Ferry, Shepherdstown, the Hollywood Casino, the Appalachia trail, the Shenandoah & Potomac Rivers, and many historical sites. Enjoy sun rise from the deck and sunsets from the porch.

Superhost
Flat in Charles Town
4.84 out of 5 average rating, 122 reviews

The Pick Me Upper in DT Charles Town near Harpers

A peaceful getaway to relax, unwind, and feel at home away from home. This third floor apt is spacious and bright with a mid-century modern and eclectic style. Private guest entrance is in the front of the house, located in the heart of downtown Charles Town. Just park your car and walk to all the local restaurants and shops! Only 10 minutes from Historic Harpers Ferry. You will fall in love with this place.

Guest favourite
A modern kitchen features sleek cabinetry and a stainless steel stove. A vibrant green wall with an illuminated neon artwork adds a pop of color. A dining table with metal chairs is positioned against the wall, creating a stylish yet functional space.
Home in Harpers Ferry
4.93 out of 5 average rating, 716 reviews

Eclectic & Romantic - Walk to Historic Downtown!

Eclectic space full of little treasures I’ve picked up during my travels. You will find the place cozy enough for a reset and recharge weekend but also inspiring for gatherings and celebrations. Take advantage of the books, games and excellent SONOS system in the house as well as outside on the patio. This place is great for music lovers and people who enjoy a change from the ordinary.

Top guest favourite
Cabin in Shepherdstown
4.96 out of 5 average rating, 519 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.

Top guest favourite
A spacious kitchen area features natural wood cabinetry and a large dining table with ample seating. Vaulted ceilings with wooden beams enhance the airy feel. A large window illuminates the room, providing views of the surrounding trees.
Chalet in Harpers Ferry
4.98 out of 5 average rating, 125 reviews

Family Reunion Escape: Warm 3BR Chalet

Experience an eco-friendly wooden chalet with a stunning fireplace and a cozy atmosphere. This retreat is perfect for those seeking relaxation, as well as adventure lovers with a variety of outdoor activities. Be sure to check out our detailed Guidebook, showcasing nearby attractions, wineries, breweries, and scenic viewpoints for an unforgettable stay.

Guest favourite
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
4.97 out of 5 average rating, 460 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.

Popular amenities for Charles Town holiday rentals

When is the best time to visit Charles Town?

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Frequently Asked Questions

  • 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.

  • How much does it cost to stay in apartment rentals in Charles Town?

    Experience the best of Charles Town with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Charles Town?

    Four-legged friends are welcome in Charles Town. Choose from more than 10 vacation rentals for guests traveling with pets.

  • 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 air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Charles Town. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Charles Town have a kitchen?

    Absolutely! We offer over 20 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 wifi?

    Absolutely! We offer over 20 house rentals with wifi 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 20 house rentals with free parking in Charles Town. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Charles Town

  • Total holiday rentals

    Explore 50 holiday rentals in Charles Town

  • Nightly prices starting at

    Charles Town holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 2,750 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Charles Town holiday rentals include wifi 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!