Holiday houses in Ridgeway

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Top-rated holiday rentals in Ridgeway

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, 475 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...

Guest favourite
The exterior of a one-story home is showcased, featuring red shutters and a white front door. A well-maintained lawn surrounds the house, with a prominent tree and colorful flowerbeds adding to the inviting curb appeal.
Home in Inwood
4.93 out of 5 average rating, 193 reviews

Lindas Country Cottage

Come and relax in our Little County Charmer If needed for extended t. Under 2 miles from Interstate. 15 min from Charlestown Casino and horse racing. JD’s Fun Center with pool for children. ..2 hrs from Massanuttan . Take a ride to Historic Berkley Springs Or Harpers ferry.. Home is in a quite neighborhood. Tv Wi-Fi. Home is close to dining and fast foods delivery. So if you wanna feel right at home while visiting or town stop by and pay a visit at our small home with a little country charm

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, 196 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, 290 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
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.
Treehouse in Shepherdstown
4.97 out of 5 average rating, 420 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.

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, 199 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
4.97 out of 5 average rating, 115 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.

Luxe
Cabin in Berkeley Springs
4.99 out of 5 average rating, 176 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
Apartment in Berkeley County
5 out of 5 average rating, 21 reviews

Private basement unit Bunker Hill, WV (WV-VA line)

Forget your worries in this private, fully furnished, spacious unit located on the WV-VA line. Follow a lighted paver path to the side gate into your own sub fence leading to the basement unit. The unit has a dorm refrigerator, microwave and 2 burner portable induction cook top for anyone wanting to cook. Our home is 5mins off of Interstate 81 and from the Amazon distribution center. We are approximately 20mins to Winchester, VA and 20mins to Martinsburg, WV.

Guest favourite
An A-Frame home is surrounded by trees, featuring a stone patio with four black lounge chairs arranged around a circular fire pit. The exterior is fitted with large windows, allowing for ample natural light.
Home in Gerrardstown
4.94 out of 5 average rating, 114 reviews

A-Frame Mountain Retreat

Seeking solace? This A-Frame home is a little slice of serenity. Come stay in a quiet and peaceful mountain community of West Virginia. The house has been fully renovated from top to bottom. It is cozy, chic and is fully equipped with everything you could possibly want or need to enjoy your time away. It's only six miles from restaurants, shops and interstate 81, but it truly feels like you are a lifetime away from the "noise" of everyday life.

Guest favourite
An open-concept kitchen and living area is presented, featuring modern cabinetry and stainless steel appliances. A cozy armchair with a blue cushion sits beside a small table, while barstools line the kitchen counter. A patterned table adds a splash of color to the space.
Townhouse in Winchester
4.92 out of 5 average rating, 303 reviews

Modern Elegance in Historic Old Town Winchester

Just a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.

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, 167 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.

Popular amenities for Ridgeway holiday rentals