Family-friendly vacation rentals in Charles Town

4.97 out of 5 average rating, 263 reviews

Cabin in Charles Town

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!

FamilyKitchenGetting around

The exterior of a custom-built home features large, angular windows that invite natural light. A stone fire pit is surrounded by log benches, ideal for gatherings. Lush greenery and shaded areas enhance the natural setting, with steps leading up to the entrance of the home.

4.9 out of 5 average rating, 126 reviews

Modern Lakehouse, Private Dock near Harpers Ferry

This custom built home on Lake Shannondale has private lake access, nestled in the low mountains of West Virginia. Wake up steps from the water, only 20 minutes from historic Harper’s Ferry and the Charlestown casino, 10 minutes from Loudoun County’s wine country and breweries, or a short drive from multiple Civil War sites. This 4-bedroom, 2.5-bath home has its own dock, outdoor fire pit, canoes/kayaks/paddle boards & spacious open layout designed for families, gatherings and celebrations.

KitchenFamilyCheck-in

Guesthouse in Charles Town

Illuminated lanterns are hung from decorative hooks among trees, casting a warm glow. The surrounding area is decorated with blooming daffodils in vibrant yellow, set against lush greenery, contributing to a peaceful outdoor setting as dusk approaches.

Coorie Inn

We are growing. Private bedroom added to make this a two full bedroom offering with kitchenette. Please come stay a spell! Perched just over the Shenandoah River (river access in multiple places) with mountain views, this getaway lets you get lost in nature with all the creature comforts of home. ***Dogs are welcome with PRIOR approval from the host. Please message me if you'd like to bring your fur bud! ***Please see additional info for all of the comforts provided! ***No smoking please.

KitchenFamilyOutdoor spaces

4.77 out of 5 average rating, 133 reviews

Treehouse in Shepherdstown

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.

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.

FamilyIndoor spacesOutdoor spaces

4.98 out of 5 average rating, 452 reviews

A spacious deck surrounds the cabin, featuring a covered gazebo and a hot tub. Decorative string lights create a gentle glow above, while the natural landscape of rocks and greenery provides a serene backdrop. The cabin's exterior showcases a welcoming design in a wooded setting.

4.96 out of 5 average rating, 138 reviews

Mountainside Retreat: Hot tub,Arcade, Theater,Pets

Imagine waking up to the gentle sound of a babbling brook as sunlight filters through the trees. Your mountain escape awaits! This charming, pet-friendly cabin offers the perfect blend of comfort and adventure. Unwind in the hot tub, roast marshmallows by one of the multiple fire pits, or embark on a hike through our private trails. Enjoy modern amenities, including a movie room and arcade games, with a touch of rustic charm. This is your home base for exploring the beauty of West Virginia.

FamilyIndoor spacesRiver

Cottage in Shenandoah Junction

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.

Modern, private cottage at Fairview Organic Farm

We did NOT raise our rates. AIRBNB has added their fees to our rate so the price you now see has their fees included. Traveling Nurses welcome. Sitting atop a hill on 23 acres at historic Fairview Organic Farm, Circa 1737, the cottage is surrounded by pasture, & history at the Harpers Ferry Gap. A few miles to Charles Town, Harpers Ferry, Shepherdstown, the Hollywood Casino, the Appalachia trail, & the Shenandoah & Potomac Rivers. Enjoy sun rise from the deck and sunsets from the porch.

Indoor spacesKitchenAmenities

4.96 out of 5 average rating, 231 reviews

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.

4.97 out of 5 average rating, 136 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.

FamilyIndoor spacesCondition

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.

Vacation home in Charles Town

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!

Indoor spacesFamilyLocation

4.91 out of 5 average rating, 127 reviews

4.94 out of 5 average rating, 232 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

Indoor spacesFamilyWifi

4.9 out of 5 average rating, 148 reviews

Home in Charles Town

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.

Indoor spacesFamilyCheckout

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.

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!

KitchenFamilyHiking

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.

4.93 out of 5 average rating, 783 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.

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Popular amenities for Charles Town family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.96 out of 5 average rating, 105 reviews

Guest-Favorite A-Frame with Hot Tub Harpers Ferry

Indoor spacesFamilyLong stay

An outdoor space features a luxurious hot tub surrounded by lush greenery. A wooden deck extends to a fire pit area, enhancing the serene setting. String lights create a warm ambiance, perfect for evening relaxation in nature.

4.99 out of 5 average rating, 201 reviews

Cozy Bear-Themed Mountain Cabin, Relaxing Hot Tub

FamilyKitchenHot tub

4.92 out of 5 average rating, 133 reviews

Mountain Luxury - Hot Tub, Amazing Views & More!

KitchenFamilySleep quality

Superhost

A large hot tub is seen nestled amongst trees, with steam rising gently from the surface. The backdrop features rolling hills and the Shenandoah River, creating a serene natural setting. The scene captures the essence of relaxation in a secluded woodland environment.

Home in Charles Town

Terra Alta - Incredible River Views and Hot Tub!

FamilyKitchenComfort

4.82 out of 5 average rating, 297 reviews

4.97 out of 5 average rating, 151 reviews

3BR Stone Cabin | Hot Tub + Firepit | Valley Views

Indoor spacesKitchenTV

A spacious backyard is surrounded by a wooden fence, showcasing a patio area with multiple seating options. A hot tub is visible, along with a fire pit and several Adirondack chairs arranged for gathering. Lush green grass and mature trees enhance the outdoor setting.

4.89 out of 5 average rating, 235 reviews

The Historic Booth House at the Harpers Ferry KOA

KitchenIndoor spacesTV

4.83 out of 5 average rating, 251 reviews

Historic Home, Hot Tub, Campfire Ring, Hardwood

KitchenFamilyParking

4.99 out of 5 average rating, 640 reviews

An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.

Cabin in Bluemont

Rustic Blue Ridge Cabins

KitchenFamilyGetting around

Family- and pet-friendly home rentals

The cabin’s exterior is softly illuminated by string lights, showcasing its rustic red wood siding. Steps lead up to a spacious deck, surrounded by lush trees, creating an inviting entrance. The path is lined with stones, enhancing the natural setting of the property.

4.96 out of 5 average rating, 220 reviews

Applemoon: Charming Log Cabin in a Mountain Lake Community

Indoor spacesKitchenWifi

5.0 out of 5 average rating, 202 reviews

A charming two-story cottage features a welcoming front door framed by decorative shutters and flower planters. A covered porch is seen to the left, adding outdoor space for relaxation. The surrounding yard is well-maintained, providing a pleasant view of the greenery.

Cottage in Shepherdstown

The Creekside Cottage: Downtown | Pet-Friendly

KitchenFamilyCheckout

4.98 out of 5 average rating, 281 reviews

The view captures the farmhouse exterior, showcasing a stone and plaster combination with a dark metal roof. Lush green vines climb the walls, and a spacious deck is visible. Surrounding gardens and pathways enhance the inviting landscape under a clear blue sky.

Farm stay in Hamilton

Ballenger Farm

FamilyKitchenView

Farm stay in Purcellville

A bright living area is presented with large windows allowing natural light to fill the space. Comfortable furnishings include a sectional sofa and a circular coffee table, while a patterned area rug adds warmth. A television is mounted on a dark cabinet, enhancing the room's functionality.

50-Acre Farmhouse Getaway Oasis in VA Wine Country

FamilyKitchenAccuracy

4.98 out of 5 average rating, 165 reviews

Vacation home in Martinsburg

An inviting entryway showcases a wooden staircase leading to a loft area. The walls are adorned with wooden paneling and a prominent 'Station' sign. A coffee station and laundry area are conveniently positioned on one side, enhancing functionality.

The Train Station Lodge

KitchenFamilyBathroom

4.95 out of 5 average rating, 112 reviews

4.94 out of 5 average rating, 220 reviews

The spa-inspired master bath features a freestanding tub with a sleek design, set against a backdrop of rich wooden tile. A wooden stool complements the space, while a glass shower enclosure and minimalist fixtures contribute to a modern aesthetic.

Home in Bolivar

Luxury, Spa tub, movie rm, new AC, best beds ever

Indoor spacesFamilyCheckout

Guest suite in Shepherdstown

Historic Scrabble, Shepherdstown

KitchenIndoor spacesHiking

4.96 out of 5 average rating, 761 reviews

4.98 out of 5 average rating, 211 reviews

The exterior of the cabin is showcased, featuring large vaulted windows that allow natural light to fill the space. The deck is furnished with a table and chairs, surrounded by a lush yard and trees displaying autumn colors.

Cabin in Gerrardstown

The Nest: Modern Cabin Retreat on 5 Wooded Acres

KitchenFamilyParks

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 289 reviews

A charming outdoor seating area features red wooden chairs and a fire pit, surrounded by lush greenery and pavers. The Cottage, with its welcoming facade and gray metal roof, is visible in the background, offering a cozy retreat in a natural setting.

Cottage in Bluemont

Cottage on Horse Farm: Wineries/Breweries, Horses!

KitchenFamilyAir conditioning

4.93 out of 5 average rating, 321 reviews

The cabin features a contemporary A-frame design with large windows that reflect surrounding trees. A spacious deck wraps around the structure, providing outdoor seating options. Natural light streams through the windows, inviting a connection with the outdoors.

Cabin in Hedgesville

Bear Pines Retreat ~ Game Room ~ Screened Porch

FamilyIndoor spacesHeating

4.98 out of 5 average rating, 102 reviews

A circular living area is surrounded by large windows that offer views of the serene woods. Comfortable seating includes a green sofa and two white chairs, complemented by a unique pendant light and a cozy rug on the carpeted floor.

Cabin in Hedgesville

Round 70s cabin-pickleball, golf, gym, pools

KitchenIndoor spacesGetting around

4.98 out of 5 average rating, 147 reviews

A log cabin is nestled among the trees, featuring a fenced inground pool in the foreground. The pool area is surrounded by a textured patio, complemented by several wooden chairs positioned nearby. The cabin is situated on a gravel driveway, highlighting its private setting.

Cabin in Fort Valley

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit

FamilyIndoor spacesQuiet

4.94 out of 5 average rating, 201 reviews

A spacious great room features a large sectional sofa in rich orange, inviting relaxation. Tall windows allow natural light to fill the space, offering views of the surrounding forest. A decorative area rug anchors the seating area, complemented by a coffee table and thoughtfully arranged decor.

Chalet in Hedgesville

Starcatcher Chalet, The Woods Resort

KitchenFamilyHot tub

Tiny home in Stephens City

Farm Stay in a luxury tiny home with hot tub

Indoor spacesKitchenValue

5.0 out of 5 average rating, 169 reviews

Farm stay in Purcellville

A horse stands peacefully in a lush green pasture, surrounded by a black wooden fence. In the background, a well-maintained barn with a cupola is visible, complemented by a clear blue sky and scattered clouds.

The Hunt Box @ Tally Yo Farm

Indoor spacesKitchenHospitality

4.98 out of 5 average rating, 243 reviews