Family-friendly holiday rentals in Charles Town

4.97 out of 5 average rating, 261 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!

FamilyKitchenSolo travel

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, 124 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.

FamilyIndoor spacesBathroom

Guest suite in Harpers Ferry

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.

4.98 out of 5 average rating, 172 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!

KitchenFamilyParking

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.

4.77 out of 5 average rating, 133 reviews

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.

KitchenIndoor spacesHiking

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.

4.98 out of 5 average rating, 448 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.

KitchenFamilyBarbecue

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, 137 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.

KitchenIndoor spacesView

Tiny home in Harpers Ferry

4.96 out of 5 average rating, 209 reviews

Romantic & Fun w/Amazing Overlook & Hot Tub

Pet Free majestic views of 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, soaking tub or taking in the beautiful scenery while enjoying a relaxing outdoor shower in our all cedar shower room.

FamilyIndoor spacesLocation

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.

4.96 out of 5 average rating, 230 reviews

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.

FamilyIndoor spacesQuiet

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!

KitchenFamilyParking

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.

FamilyIndoor spacesParking

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!

KitchenIndoor spacesGetting around

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

4.82 out of 5 average rating, 297 reviews

Terra Alta - Incredible River Views and Hot Tub!

MOUNTAIN MAMA VACATION HOMES & CABINS A huge hot tub, stunning hilltop views, the sound of rushing rapids below--this place has it all! On 3+ acres of private woodland set high on a hill overlooking the Shenandoah river, this large river house can accommodate many guests and is just 15-20 min from tons of attractions: whitewater rafting, historic Harpers Ferry, Virginia wine country, and more.

KitchenIndoor spacesBarbecue

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, 104 reviews

Guest-Favorite A-Frame with Hot Tub Harpers Ferry

Indoor spacesFamilyHospitality

4.92 out of 5 average rating, 132 reviews

Mountain Luxury - Hot Tub, Amazing Views & More!

KitchenIndoor spacesAccuracy

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, 130 reviews

Gorgeous cabin on Blue Ridge

Indoor spacesKitchenDecor

4.83 out of 5 average rating, 252 reviews

Hot Tub, Historic, Rural Setting, Convenient

FamilyKitchenDecor

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

FamilyIndoor spacesLayout

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, 199 reviews

Cozy Bear-Themed Mountain Cabin, Relaxing Hot Tub

FamilyIndoor spacesParking

4.96 out of 5 average rating, 183 reviews

The timber-framed chalet is surrounded by vibrant flower gardens, showcasing various colorful blooms. Large windows and a balcony enhance the exterior, framed by trees creating a natural backdrop. A patio area with seating is visible in the foreground, inviting guests to enjoy the peaceful surroundings.

Guesthouse in Hamilton

Trailside Chalet (A storybook chalet with hot tub)

FamilyKitchenCheckout

An aerial view showcases the expansive Potomac River surrounded by lush greenery and rolling hills. The property features a large grassy area leading to the river's edge, set against a backdrop of dense trees and distant mountains.

4.93 out of 5 average rating, 183 reviews

Riverfront HarpersFerry! PrivateDock,HotTub,Kayaks

Indoor spacesFamilyHospitality

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.

4.97 out of 5 average rating, 218 reviews

Applemoon: Charming Log Cabin in a Mountain Lake Community

Indoor spacesKitchenCheck-in

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, 777 reviews

Eclectic & Romantic - Walk to Historic Downtown!

FamilyIndoor spacesBackyard

4.98 out of 5 average rating, 208 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

KitchenFamilyAccess

Guest suite in Shepherdstown

4.96 out of 5 average rating, 759 reviews

Historic Scrabble, Shepherdstown

FamilyKitchenEV charging

4.98 out of 5 average rating, 280 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

KitchenFamilyAmenities

Apartment in Shepherdstown

The open kitchen features dark cabinetry and modern appliances, including an oven and refrigerator. A round dining table with two bar stools is positioned nearby. A patterned area rug and two coffee tables add a cozy touch to the living space, with warm wood flooring throughout.

4.96 out of 5 average rating, 458 reviews

Downtown: Explore Shepherdstown from cozy 1br apar

Indoor spacesFamilyBathroom

4.95 out of 5 average rating, 287 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!

KitchenFamilyComfort

4.92 out of 5 average rating, 407 reviews

The cottage is a charming two-story building, featuring a dark exterior with large windows. A welcoming porch is accented by steps leading to the entrance, and a stone pathway guides through the lush green yard, surrounded by trees.

Cottage in Leesburg

The Cottage at Forest Hills Farm

KitchenIndoor spacesCheckout

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 115 reviews

Farm stay in Bluemont

The Cottage at Nestled Inn

FamilyKitchenBreakfast

4.93 out of 5 average rating, 199 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

Indoor spacesKitchenNearby

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.

4.98 out of 5 average rating, 240 reviews

The Hunt Box @ Tally Yo Farm

Indoor spacesKitchenGetting around

5.0 out of 5 average rating, 109 reviews

A spacious solarium features large windows allowing plenty of natural light to fill the room, with views of the surrounding greenery. A comfortable seating area is arranged with a mix of sofas and chairs, complemented by various plants adding a touch of nature. The heated concrete floor enhances comfort in this inviting gathering space.

Home in Knoxville

An Escape Bordering National Park land 1 mi to C&O

FamilyIndoor spacesBeach

4.98 out of 5 average rating, 143 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

Indoor spacesKitchenHiking

5.0 out of 5 average rating, 110 reviews

A rustic outdoor seating area features log benches arranged around a circular fire pit. The red chalet with a flag is visible in the background, surrounded by trees shedding their leaves. A gravel pathway connects the seating area and the chalet.

Chalet in Hedgesville

Cherry Run Chalet

Indoor spacesKitchenWalkability

4.82 out of 5 average rating, 129 reviews

A wooden deck extends from the cabin, surrounded by lush green trees. A striped awning provides shade over a picnic table, creating a space for outdoor dining or relaxation. The natural ambiance enhances the secluded feel of the property.

Cabin in Keedysville

Quiet Antietam Cabin

FamilyIndoor spacesLocation