Family-friendly holiday rentals in Charles Town

4.98 out of 5 average rating, 245 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!

Tiny home in Harpers Ferry

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.

4.96 out of 5 average rating, 179 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.

Tiny home in Harpers Ferry

The cabin is nestled among vibrant greenery, surrounded by flowering plants and lush trees. A garden trellis adorned with blooms contrasts with the cabin's rustic exterior, which features a screened porch elevated off the ground. Natural pathways guide the way through the tranquil garden setting.

4.97 out of 5 average rating, 573 reviews

Retro Tiny Cabin in the Trees

Glamping in Harpers Ferry! Elevated 8' x 16' cabin in a lush garden property surrounded by trees. Full bathroom w/rain showerhead. King bed can be converted to 2 twins if requested. 1940s vintage decor. Minifridge, microwave, toaster, coffeemaker, elec kettle, minigriddle. NO STOVE. Opens to an 8' x 16' screened porch w/ceiling fan, comfy seating, kitchen table & sink. Private spot yet in walking distance to many HF activities & dinner restaurants. Indoor/outdoor living & in-town convenience.

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.

4.99 out of 5 average rating, 144 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!

4.98 out of 5 average rating, 118 reviews

Cabin in Harpers Ferry

Sunset Lion Mountain Cabin near a Lake & Vineyards

Relax to the mountain breeze and sounds of nature in this cozy cabin. Located 1 mi to the Appalachian Trail, 3 min drive to the lake and a 15 min drive to Charles Town & vineyards. Enjoy spectacular sunset views from the expansive front deck, living and dining rooms, firepit and hammock. Enjoy the propane grill, outdoor table & chairs and firepit. Unwind in the living room with vaulted ceilings, recliners and games. Downstairs bedroom and bathroom, upstairs includes one bedroom and a loft.

Guest suite in Harpers Ferry

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.

5 out of 5 average rating, 273 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.

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.

4.97 out of 5 average rating, 380 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.

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, 494 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.

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, 213 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

A cozy living area features a comfortable daybed adorned with soft pillows. A desk with a chair is positioned near a window, complemented by a decorative wreath. A television is situated on a light-colored media console, with a patterned rug adding warmth to the space.

Apartment in Charles Town

4.84 out of 5 average rating, 121 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.

4.93 out of 5 average rating, 704 reviews

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

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.

4.96 out of 5 average rating, 513 reviews

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

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.

Popular amenities for Charles Town family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 206 reviews

The unique dome structure is surrounded by lush trees, featuring large windows and a cozy entrance. An inviting outdoor seating area with a fire pit and black chairs is positioned on the wraparound deck, accompanied by a hammock and a hot tub.

Dome in Mercersburg

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

4.89 out of 5 average rating, 236 reviews

A private hot tub is positioned on a wooden deck, surrounded by trees and greenery. The view of the distant landscape is visible, with soft colors of nature reflecting a serene atmosphere. Soft lighting fixtures hang from the roof, adding to the inviting space.

Cabin in Gerrardstown

Modern Eclectic Treetop Cabin With Hottub

5 out of 5 average rating, 100 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

4.98 out of 5 average rating, 164 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)

A charming exterior view of a cabin-style home is presented, featuring a welcoming porch with black railings and lantern-style lights. The house is surrounded by trees, with warm light streaming from the large windows, creating a sense of comfort and connection to nature.

4.99 out of 5 average rating, 121 reviews

Whiskey Acres | Modern Cabin w/ Hot Tub, Axes, etc

Guest suite in Winchester

A spacious family room with soft carpet features a large flat screen TV mounted on the wall. A rustic wooden table with two stools is positioned nearby. Poster art from classic movies adorns the walls, while natural light filters in through the window.

4.97 out of 5 average rating, 238 reviews

Full basement with private entrance. Hot tub

A gravel area features several rustic wooden chairs arranged around a stone fire pit, with a gentle fire burning. Soft string lights illuminate the space, enhancing the cozy atmosphere. The exterior of the cabin is visible in the background, surrounded by trees.

4.94 out of 5 average rating, 159 reviews

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

A log cabin features a stone chimney and a spacious front porch with a wooden railing. Surrounded by vibrant autumn foliage, the lower level offers a clear view of the landscaped yard, leading to the area with Adirondack chairs, inviting guests to relax outdoors.

4.93 out of 5 average rating, 104 reviews

Charming log cabin by Berkeley Springs (+ hot tub)

Family- and pet-friendly home rentals

Guest suite in Sharpsburg

A bright and modern living area is highlighted by two red accent chairs and a comfortable sofa. A coffee table sits centrally, with a television mounted on the wall. Natural light filters in through large windows, enhancing the inviting space.

4.94 out of 5 average rating, 278 reviews

Guest Apartment by C & O Canal and Battlefield

4.94 out of 5 average rating, 259 reviews

A two-story cottage is set amidst lush greenery, featuring a large upper deck that offers views of the surrounding woods. Colorful azaleas and shrubs enhance the entrance, while a gravel drive leads to the property, surrounded by trees exhibiting signs of spring.

Guesthouse in Myersville

Spruce Run Cottage, Farm stay on Catoctin Mountain

4.94 out of 5 average rating, 418 reviews

A charming multi-story home features a light-colored wooden exterior, complemented by stone pathways and a staircase. Flags adorn the exterior, and a spacious deck area is visible, surrounded by greenery. The building's architectural details showcase a blend of historical and modern design.

Home in Harpers Ferry

Gayte House Gay Owned, Liberal Oasis

Superhost

A well-maintained exterior showcases a brick building with a white double door entrance. Surrounding greenery includes manicured lawns and bushes, enhancing the natural setting. The entrance is easily accessible, providing a welcoming approach to the ground-level unit.

Home in Inwood

4.87 out of 5 average rating, 703 reviews

Arden House, Inwood WV

4.91 out of 5 average rating, 354 reviews

The living area features a pull-out futon in front of a patterned area rug. Two wooden chairs are positioned at a small table beside a large window, with a vibrant artwork depicting a barn mounted on the wall. A kitchenette area is visible in the background.

Home in Knoxville

Outdoor Basecamp at Tiny Hidden Ridge

4.97 out of 5 average rating, 115 reviews

A living room is presented with a navy blue sectional sofa adorned with white pillows. Framed artwork lines the walls, complementing the hardwood floors. A round glass coffee table sits in the center, beside a decorative area rug. Natural light enters through the window, enhancing the space.

Apartment in Winchester

Historic Wisteria House on Old Town Walking Mall

4.95 out of 5 average rating, 190 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

Snow tubing nearby, spa tub movie room best beds

4.91 out of 5 average rating, 377 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

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 111 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

5 out of 5 average rating, 112 reviews

A circular fire pit is surrounded by six gray Adirondack chairs, set on gravel. Beyond, a spacious wooden deck is visible, featuring a covered area and a picnic table. The yard is fenced with trees providing a natural backdrop.

Home in Hedgesville

Spacious Retreat for Groups, Well Stocked

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.

4.93 out of 5 average rating, 294 reviews

Bear Pines Retreat ~ Game Room ~ Screened Porch

The living area features large two-story windows that offer views of the surrounding wooded landscape. A cozy leather sofa and armchair are complemented by a wooden dining table with seating for six. Warm lighting and natural textures enhance the inviting atmosphere.

5 out of 5 average rating, 111 reviews

Cozy Secluded A-Frame Cabin Retreat

4.95 out of 5 average rating, 407 reviews

A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.

Cottage in Hamilton

*Cottage @ Firefly Cellars* VA Wine Country escape

5 out of 5 average rating, 148 reviews

A warm interior features a spacious bed dressed in a rich, burgundy coverlet, complemented by wooden wall panels and exposed beams. A cozy seating area is provided next to the bed, with light streaming in from a window adorned with wooden shutters.

Cabin in Delaplane

Herb Cottage-Elegant Cabin plus Optional Farm Tour

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, 208 reviews

The Hunt Box @ Tally Yo Farm

A charming cabin is nestled among lush trees, featuring a spacious deck that overlooks the surrounding greenery. The structure highlights a gabled roof and large windows, inviting natural light into the house. The forested setting enhances the feeling of seclusion and tranquility.