Holiday houses in Charles Town

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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 $67 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Charles Town holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Charles Town rentals

  • 4.9 Average rating

    Charles Town stays are highly rated by guests—averaging 4.9 out of 5!

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
4.97 out of 5 average rating, 261 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
5.0 out of 5 average rating, 49 reviews

Gaming Gazebo, Hot Tub, Sauna, Cold Plunge & Golf

The Fox Den is modern luxury in a wilderness hide away. Here, you can unwind in comfort enjoying a quiet woodland setting. Access connector trails to the Appalachian Trail from the front door. Visit historic Harpers Ferry. Tour wineries and breweries. Try your luck at the Hollywood Casino. Relax and enjoy a hot tub sunset, unwind fireside with s'mores, play board games in this cozy cabin.  The Fox Den is a retreat for the senses, and a place to make wonderful memories with family and friends.

Guest favourite
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
4.98 out of 5 average rating, 445 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 favourite
A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.
Home in Harpers Ferry
4.97 out of 5 average rating, 128 reviews

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.

Superhost
A pathway lined with trees leads towards the river, while a spacious deck equipped with outdoor seating is visible. The deck is constructed of wooden planks, providing a view of the natural surroundings. A grill is placed nearby, adding to the outdoor amenities.
Holiday home in Charles Town
4.91 out of 5 average rating, 126 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!

Top Guest favourite
Home in Harpers Ferry
4.93 out of 5 average rating, 223 reviews

Cozy Tiny House in Harpers Ferry Tub & River Views

Pet Free, 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, 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

Guest favourite
Home in Charles Town
4.9 out of 5 average rating, 147 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.

Guest favourite
An open-concept living area features a blue sofa and a brown armchair arranged around a patterned area rug. A wooden coffee table and floor lamp add warmth, while a TV is mounted on the wall. Dining space and kitchen are visible in the background.
Home in Harpers Ferry
4.97 out of 5 average rating, 127 reviews

Relaxing Getaway Near Shenandoah River Access

Come and enjoy our spacious 3bd/2ba home in Harpers Ferry, WV just across the Virginia state line and close to many local attractions! Perfect for families featuring a large fenced in backyard. Centrally located within 15 mins from historic Harpers Ferry; within 1/2 mile of public boat access to the Shenandoah River; 2 miles to Appalachian Trail; less than 15mins to numerous breweries & wineries; 10mins to Charles Town Casino. Enjoy all this wonderful area has to offer!

Guest favourite
An A-frame cabin is surrounded by trees, featuring large front windows that invite natural light. A spacious wrap-around deck includes cozy seating, a hot tub, and a fire pit. The warm glow from the interior highlights the modern design and inviting atmosphere.
Cabin in Harpers Ferry
4.96 out of 5 average rating, 102 reviews

Guest-Favorite A-Frame with Hot Tub Harpers Ferry

Our guests tell us: "We didn't want to leave." Slip into the salt-water hot tub under the stars, enjoy movie night on the TV screen projector with Bose soundbar system, and watch the A-frame windows fill with morning light. The cabin is nestled in a mountain community in Shannondale — 6 min from the Shenandoah River, 20 min from the Appalachian Trail and Historic Harpers Ferry, and 90 min from DC. ★ 4.95 Guest Favorite · Superhost

Top Guest favourite
Cabin in Front Royal
4.99 out of 5 average rating, 451 reviews

Mountaintop Retreat with Wood Fired Hot Tub

Doah House is a private retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. A calm container for rest and observation, the pace softens, shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing the light, the air, the sound. Each day feels different. The forest shifts, and you might, too.

Top 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
4.94 out of 5 average rating, 773 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.

Superhost
A spacious bedroom is illuminated by natural light from two large windows. A comfortable bed is styled with soft linens and a warm blanket. Two armchairs sit invitingly in the corner, and textured rugs decorate the hardwood floor.
Apartment in Charles Town
4.8 out of 5 average rating, 114 reviews

Spacious apt with King beds in DT Charles Town

Welcome to our charming 2-bedroom Airbnb in downtown Charles Town, WV! This modern retreat offers two spacious bedrooms with king-size beds for a comfortable stay. Explore the city's attractions and enjoy a cozy night's sleep in stylish accommodations. Book now for a memorable stay in the heart of Charles Town!

Popular amenities for Charles Town holiday rentals

When is the best time to visit Charles Town?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$257 NZD$222 NZD$244 NZD$218 NZD$244 NZD$215 NZD$203 NZD$227 NZD$237 NZD$228 NZD$281 NZD$250 NZD
Avg. temp1°C3°C7°C13°C18°C23°C25°C24°C20°C14°C8°C3°C

Frequently Asked Questions

  • What are the best places to stay in Charles Town?

    Charles Town has a mix of historic downtown residences, quiet residential neighborhoods, and rural retreats surrounded by countryside. Many travelers choose homes near the town center for easy access to local cafes, shops, and heritage sites.

  • What are the best things to do in Charles Town with kids?

    Families often explore local parks, interactive museums, and seasonal fairs around Charles Town. Visiting hands-on history centers or enjoying outdoor areas is frequently suggested for a relaxed, engaging day.

  • What are some of the best things to do in Charles Town?

    Explore the Charles Town Historic District, visit museums focused on local history, and enjoy entertainment venues around town. Outdoor enthusiasts frequently head to nearby trails or green spaces for fresh air.

  • How is the weather in Charles Town?

    Charles Town has cold winters, with January temperatures averaging 25–43°F (-4–6°C), and warm, humid summers reaching 67–88°F (19–31°C) in July. Spring and autumn bring mild afternoons, while rainfall peaks in late spring.

  • When is the best time to visit Charles Town?

    Late spring and early autumn are often recommended for comfortable temperatures, lower humidity, and colorful scenery. Many visitors enjoy the area during annual fairs or when outdoor festivals take place.

  • What are the best places to visit in Charles Town?

    The Charles Town Historic District, local museums, and cultural sites are frequently suggested for learning about the area’s past. Visitors also enjoy exploring green spaces and public art installations.

  • What are some hiking trails in Charles Town?

    Charles Town has access to several nature trails and wooded paths, often found within regional parks or conservation areas. These routes are popular for birdwatching, gentle walks, and family outings.

  • What are some family activities we can do in Charles Town?

    Families enjoy strolling through local parks, visiting interactive heritage exhibits, or attending community fairs and outdoor concerts in Charles Town. Seasonal events often include craft activities suitable for all ages.

  • What are some of the best day trip ideas from Charles Town?

    Many visitors explore historic towns, national parks, or scenic overlooks around Charles Town. Wine country tours, river activities, and nearby cultural sites are also frequently suggested for a day adventure.

  • Are there any pet friendly accommodations available in Charles Town?

    Pet-friendly vacation rentals are available in and around Charles Town, especially in the downtown and countryside areas. Many local parks also make it convenient to spend time outdoors with your pet.

  • What are some local tips for visiting Charles Town?

    Consider exploring early in the day to enjoy quieter streets and a relaxed atmosphere. Locals know that weekend markets and seasonal fairs offer a taste of the community’s traditions and flavors.

  • What is Charles Town known for?

    Charles Town is known for its historic downtown, connections to early American history, and regional markets. The area often draws visitors interested in heritage architecture and nearby outdoor recreation.

  • What are the best hidden gems to explore in Charles Town?

    Explore smaller local museums, artisan shops, or quiet garden spaces tucked around Charles Town. Often, less-traveled walking trails and locally owned cafes reveal unique stories from the area.

  • What are the best foods to try in Charles Town?

    Local menus feature Appalachian-inspired dishes, homestyle pies, and fresh produce from regional farms. Country-style breakfasts, barbecue, and traditional desserts are frequently suggested for a taste of the area.

  • What should I bring for a trip to Charles Town?

    Pack comfortable walking shoes, layers for changing temperatures, and a rain jacket, as weather can shift between cool mornings and warmer afternoons. A reusable water bottle and sun protection are often useful for outdoor activities.

  • What is the nightlife in Charles Town like?

    Nightlife in Charles Town centers around live music, local pubs, and social spaces with casual dining. Evenings may include community performances, trivia nights, or events at heritage venues.

  • What are the most popular events or festivals in Charles Town?

    Charles Town hosts seasonal fairs, agricultural festivals, and cultural celebrations, often on holiday weekends or in late summer. Community parades and live music events are also popular during warmer months.

  • Are there family friendly vacation rentals in Charles Town?

    Charles Town has many family-friendly vacation rentals with spacious living areas, kitchens, and outdoor spaces, especially in residential neighborhoods. Several options offer amenities like play yards or easy access to parks.