Family-friendly holiday rentals in Shannondale

5 out of 5 average rating, 262 reviews

The treehouse is elevated among the trees, featuring large windows that offer views of the surrounding forest. The exterior is constructed with dark wood shingles and is supported by sturdy stilts, blending seamlessly with the natural environment.

Treehouse in Waterford

Hummingbirds Hideaway Treehouse

Do not book on airbnb and ask for early arrival. experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun this slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please message us prior to booking

4.9 out of 5 average rating, 115 reviews

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.

Home in Harpers Ferry

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.

4.99 out of 5 average rating, 609 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

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd of an Acre with access to wooded a trail featuring Cold Springs. Amenities-4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail,Shenandoah River, with restaurants, breweries, distilleries, and wineries close by! These are rustic not luxurious Cabins

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, 157 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, 124 reviews

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.

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.

4.98 out of 5 average rating, 120 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.

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.

4.99 out of 5 average rating, 288 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, 412 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.

4.96 out of 5 average rating, 103 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.

Home in Harpers Ferry

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.

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, 205 reviews

Applemoon: Charming Log Cabin in a Mountain Lake Community

Applemoon is a dog-friendly 1960s log cabin nestled on an acre of the Blue Ridge Mountains. 2 bedrooms with Smart TVs, a porch with hanging daybed and bistro table, and a cozy game loft will give you plenty of space to relax. Outside, enjoy dinner on the huge deck or build a fire and don't forget to look up at the night sky! Applemoon strikes the perfect balance between rustic charm and comfort while maintaining your immersion in the peaceful mountain woodlands of Harpers Ferry.

Cabin in Berkeley Springs

A modern black structure is nestled among trees, illuminated by soft sunlight filtering through the leaves. A gentle slope leads to a walkway, providing accessible entry. Nearby, a circular seating area with chairs invites relaxation amidst the natural surroundings.

4.99 out of 5 average rating, 170 reviews

Monte Vista~Golf~Views~PS5~Sport Court~EV Charger

IG @montevistawv Luxury Getaway Professionally Designed for STR 🏔️Massive Panoramic 3 State View 🏌️‍♂️Golf Ball Driving Range 🏀 Pickleball, Basketball, Volleyball & Tennis 🎮 PlayStation 5 Mini Disc ♨️ 6-Person Hot Tub 🔊Sonos Sound Throughout 🔋Level 2 EV Charger 🥾 Hiking Trail on site 🌳 33 private acres, no quiet hours 🔥 Massive Firepit + Grill & Pizza Oven 🛋️ Cozy Gas Fireplace 🌐 Fast WiFi & Three 65" Smart Tvs 🛏️ 3 King Beds & Twin Bunk Bed 💼 Dedicated Work Area

Superhost

4.81 out of 5 average rating, 463 reviews

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

MOUNTAIN MAMA VACATION HOMES & CABINS The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out or detox in the sauna. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for everyone!

Popular amenities for Shannondale family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior of a two-story house is shown, framed by tall trees and greenery. A welcoming front porch is adorned with hanging plants. A stone pathway leads to the main entrance, and a gravel driveway extends alongside the house, providing ample parking.

4.89 out of 5 average rating, 183 reviews

Mountain Cabin in the Woods, Near Wineries & More

4.99 out of 5 average rating, 394 reviews

A hot tub is situated on a deck surrounded by trees, with sunlight filtering through the branches. A pink float is placed beside the tub. The calming water reflects the warm light, creating a serene atmosphere.

Guest house in Bluemont

Skyhorse Retreat Guest House

4.95 out of 5 average rating, 414 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

4.98 out of 5 average rating, 174 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.

Guest house in Hamilton

Trailside Chalet (A storybook chalet with hot tub)

4.96 out of 5 average rating, 223 reviews

An A-frame cabin nestled among trees features a wrap-around deck overlooking the landscape. The kitchen showcases modern appliances and a spacious counter with bar stools, while a gentle waterfall flows over rocks nearby, surrounded by lush greenery.

Cabin in Bentonville

Timber Creek: Falls - A Shenandoah Cabin

4.99 out of 5 average rating, 469 reviews

An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.

Cottage in Winchester

COZY+SEXY Private Country Escape! HOT TUB & Views~

4.93 out of 5 average rating, 187 reviews

The exterior of the retreat features large glass windows, providing an open view of the surrounding landscape. A spacious deck includes two black Adirondack chairs and a private hot tub, set against a backdrop of mountains and a colorful sunset.

Cabin in Shenandoah

Blue Ridge Retreat 2 w/ Hot Tub/Sauna/Cold Plunge!

5 out of 5 average rating, 109 reviews

Farm stay in Bluemont

The Cottage at Nestled Inn

Family- and pet-friendly home rentals

Place to stay in Bentonville

A rustic cabin is illuminated by warm golden light from its windows, set against a soft twilight sky. The log exterior reflects the vintage charm of the structure, while the surrounding trees create a serene atmosphere, inviting guests to relax on the front porch.

4.99 out of 5 average rating, 523 reviews

John Pope Cabin Browntown Va. We now have Starlink

4.94 out of 5 average rating, 743 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!

A spacious living area features large windows allowing natural light to fill the room. A modern blue sofa with decorative pillows is arranged around a circular coffee table, complemented by an area rug. A stone fireplace and wall-mounted television add warmth to the space.

4.9 out of 5 average rating, 187 reviews

Bright A-frame nestled against 700 acres of forest

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, 221 reviews

The Hunt Box @ Tally Yo Farm

5 out of 5 average rating, 119 reviews

The exterior of a red brick building is shown, featuring a striking peaked roof and multiple windows. A shaded porch is visible at the entrance, adorned with potted plants. Lush greenery surrounds the property, and a gravel path leads up to the structure.

Farm stay in Leesburg

The Forge on Sunnyside Farm

4.84 out of 5 average rating, 232 reviews

A well-maintained grassy area is surrounded by lush trees, providing a serene backdrop. A stone structure with a sloped roof is visible to the side, complementing the natural landscape. A wooden fence accents the property, enhancing the sense of seclusion.

Cottage in Purcellville

Stone School House - Minutes from Harper's Ferry

4.99 out of 5 average rating, 147 reviews

Cabin in Wardensville

Sugar Maple Chalet - 67-Acre Farm

4.98 out of 5 average rating, 272 reviews

The historic Quaker colonial farmhouse, established in 1753, features a stone exterior with white trim and a large front porch. The structure displays a balanced symmetry, with multiple windows reflecting the natural surroundings, surrounded by lush greenery and a spacious lawn.

Farm stay in Hamilton

Ballenger Farm

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 127 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, 102 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

4.88 out of 5 average rating, 102 reviews

An indoor heated saltwater pool is surrounded by large windows allowing natural light to fill the space. Comfortable seating is provided by several dark wood adirondack chairs arranged neatly around the pool area, with a serene outdoor view visible through the expansive glass panes.

Home in Big Pool

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr

5 out of 5 average rating, 123 reviews

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.

Cabin in Hedgesville

Cozy Secluded A-Frame Cabin Retreat

4.93 out of 5 average rating, 133 reviews

A spacious pool area features a heated in-ground pool and spa surrounded by lounge chairs. A well-maintained lawn and shaded seating areas complement the outdoor space, while a house is visible in the background, nestled among the trees.

Home in Marshall

Clean 5BR w Heated Pool, Spa - Horse, Wine Country

4.95 out of 5 average rating, 147 reviews

Home in Adamstown

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

4.97 out of 5 average rating, 178 reviews

An outdoor deck illuminated at night features comfortable seating arranged around a fire table. A large umbrella is positioned over the dining area, and the house is adorned with soft string lights. The surrounding trees provide a natural backdrop to the inviting space.

Chalet in Hedgesville

All Seasons Retreat - Screened Porch - Fire Pit