Holiday houses in Lake Holiday

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Top-rated holiday rentals in Lake Holiday

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.99 out of 5 average rating, 469 reviews

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

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Top Guest favourite
A cozy living space features a wooden ceiling and light-colored walls. A small electric fireplace is placed beneath a wall-mounted television. A coffee table sits centrally, surrounded by two comfortable chairs and a couch, with a front door visible to the side.
Cabin in High View
4.97 out of 5 average rating, 192 reviews

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

Top Guest favourite
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.
Guest suite in Harpers Ferry
4.99 out of 5 average rating, 287 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.

Top Guest favourite
A spacious living area features vaulted ceilings with large windows allowing natural light to fill the room. A comfortable sofa faces a central coffee table, with a dining area containing a round table and chairs nearby. Shelving units display books and decorative items, enhancing the inviting space.
Cabin in Gerrardstown
4.97 out of 5 average rating, 196 reviews

Cozy Chalet Near Berkeley Springs & Harpers Ferry

The Nest is a chalet-style cabin tucked into the tree-lined mountains of Berkeley County, WV. It offers adventure, a quiet retreat & good family fun. With 5-acres in the mountainside, you'll enjoy star studded skies on clear nights & wake up to birds singing & deer wandering, with mountain views through vaulted windows. The Nest is near Martinsburg, Berkeley Springs, Harpers Ferry, Shepherdstown, Charles Town & Cacapon State Park, among other go-to destinations on the Eastern Panhandle.

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
4.96 out of 5 average rating, 101 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.

Top Guest favourite
Cabin in Grantsville
4.95 out of 5 average rating, 111 reviews

Riverfront Sauna! Hot Tub! Luxury Romantic Retreat

River views from your cozy king bed or fireside couch, sitting in the hot tub with the sounds of the river just yards away, soaking tub with bath bombs, a chandelier and mood lighting, high end espresso machine and finishes, sound appealing?? Riverside Romance offers all this and MORE! Nestled in the dreamy pines by the river, this couples escape was designed for you and your partner to escape the world and reconnect in Luxury. Surprise your significant other with a getaway to remember!

Top Guest favourite
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.
Cabin in Berkeley Springs
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

Top Guest favourite
A classic A-frame cabin is surrounded by trees, featuring a spacious deck with comfortable lounge seating. Soft lighting accentuates the inviting outdoor space, while large glass doors provide a glimpse into the cozy interior. The modern roof complements the rustic wooden facade.
Cabin in Front Royal
4.96 out of 5 average rating, 291 reviews

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

Top Guest favourite
Cabin in Great Cacapon
4.95 out of 5 average rating, 273 reviews

Walk in the clouds Cabin

Amazing veiws! This cozy cabin over looks the Potomac river valley and Greenridge state forest. You can see mountain ranges from 3 different states. Enjoy the wilderness of West Virginia with only a short drive from, D.C. and Baltimore. Just 13 miles from Berkeley springs and famous PawPaw tunnel. Perfect couple getaway. Have a bigger family? Check out our sister cabin "Hummingbird Ridge" right down the road or book both. We look forward to having you on the mountain!

Top Guest favourite
A modern cabin is set amongst lush greenery, featuring a dark exterior and a welcoming front porch. Surrounding landscaping includes a variety of shrubs and trees, creating a peaceful atmosphere. The driveway leads to the entrance, providing easy access to the secluded retreat.
Cabin in Star Tannery
4.96 out of 5 average rating, 275 reviews

Cabin With Wood Burning Hot Tub

Escape to our modern cabin on 12 private acres. Unwind in the wood-burning hot tub, embracing the surroundings and stars at night. With a contemporary design and natural light, this retreat blends with nature. Explore private trails throughout the property, enjoying nature and the fresh air. Inside, find comfort in the fully equipped kitchen and cozy living area. Perfect for a peaceful getaway, our secluded home provides privacy and relaxation.

Top Guest favourite
A modern cabin exterior is shown, featuring a sloped roof and large windows that allow natural light to fill the interior. A spacious deck is visible, furnished with two lounge chairs and a wooden rocking chair, surrounded by vibrant autumn foliage.
Cabin in Winchester
4.95 out of 5 average rating, 161 reviews

Foxtrot Mokki | Secluded Getaway 2 Hours from DC

Welcome to The Foxtrot Mokki—a Nordic-inspired retreat just two hours from DC and Baltimore. Solitude is signature. Nestled on seven secluded acres with rain-fed streams, our cozy cabin is designed for tranquility and connection with nature. Located between Old Town Winchester, VA, and Berkeley Springs, WV, it's the perfect outpost for exploring the Northern Shenandoah Valley—from charming towns to scenic hikes and wineries.

Guest favourite
A modern cabin is nestled among trees, featuring a sleek design with large windows that allow light to emanate from within. The surrounding rocky terrain is softly illuminated by exterior lighting, creating a calm ambiance in the early evening fog.
Cabin in Front Royal
4.99 out of 5 average rating, 422 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.

Popular amenities for Lake Holiday holiday rentals