Vacation rentals in Gerrardstown

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Top-rated vacation rentals in Gerrardstown

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Top guest favorite
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, 471 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 favorite
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, 733 reviews

Arden House, Inwood WV

Ground level two room unit. No steps. Separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed, sofa and full refrig.. In a separate living area, there is a queen bed, TV, bathroom, desk, table, microwave, convection oven, air fryer, gas fireplace. No oven. Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic

Guest favorite
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
4.94 out of 5 average rating, 189 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 favorite
Home in Winchester
4.98 out of 5 average rating, 218 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Top guest favorite
Treehouse in Shepherdstown
4.97 out of 5 average rating, 413 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 favorite
An airy living space features tall vaulted windows that allow natural light to fill the room. A cozy seating arrangement with a sectional sofa is positioned around a wooden coffee table. A dining area with a round wooden table is set for meals, overlooking the lush outdoors.
Cabin in Gerrardstown
4.97 out of 5 average rating, 197 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 favorite
An inviting living area showcases a yellow leather couch, positioned next to a rustic stone fireplace. A wooden beam stretches overhead, accenting the log cabin walls. Books are neatly arranged on shelves, while a patterned area rug adds texture and warmth underfoot.
Cabin in Hedgesville
4.94 out of 5 average rating, 117 reviews

Charming log cabin by Berkeley Springs (+ hot tub)

Get the most out of wild & wonderful West Virginia in this newly-renovated log cabin 20 minutes from downtown Berkeley Springs. Enjoy the wooded views from the expansive front porch, make s'mores around the stone fire pit, soak in the hot tub in the enclosed sun room, curl up with a book in front of the wood-fired stove, and get cozy in the movie theatre-like loft. You will have access to a private lake and incredible hiking trails minutes from the cabin.

Top guest favorite
An open living space features a cozy green sofa and a modern dining table with gold accents. A loft bedroom is visible above, showcasing a comfortable bed and soft bedding. Natural light pours in through large windows, highlighting the wooden elements and inviting decor.
Tiny home in Mercersburg
4.98 out of 5 average rating, 193 reviews

Boxed Inn ~ Hot Tub ~ Fire Pit

This charming, tiny home offers the perfect blend of cozy comfort and the great outdoors, all while nestled close to the Whitetail Resort. Inside is an open space bathed in natural light, where modern style meets mountain tranquility. The interior, with its thoughtfully designed features, comes with a comfortable loveseat, a smart TV, and bar seating: perfect for those intimate conversations or just catching up after a busy day on the trails.

Guest favorite
An A-Frame structure is illuminated by warm outdoor string lights, creating a cozy ambiance. Two black chairs are positioned on a stone patio in front of the house, surrounded by nature. The entrance features a large window, providing a welcoming view of the outdoors.
Home in Gerrardstown
4.94 out of 5 average rating, 113 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.

Top guest favorite
A private patio features two wooden reclining chairs positioned on a patterned rug. A wood-burning hot tub is nestled to one side, surrounded by lush greenery. String lights hang overhead, providing a subtle illumination against the backdrop of a clear blue sky.
Cabin in Star Tannery
4.96 out of 5 average rating, 279 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.

Guest favorite
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
4.89 out of 5 average rating, 242 reviews

Hottub with Valley Views ~ Romantic, Cozy

Our cabin in the treetops is the perfect place to rest, work remotely, or use as a basecamp for exploring the surrounding area. The cabin has many modern conveniences including an eco-friendly hot tub with epic views, high speed internet and chromecast for streaming your connected devices. Hot tub is available year round and safe for max of 2 adults due to its location on the upper deck. Pellet stove is available Oct-March.

Guest favorite
A rustic cottage features weathered wood siding and a welcoming front door. Two chairs sit on a circular brick patio, surrounded by colorful potted plants and neatly trimmed hedges. Lush greenery is visible in the background, enhancing the tranquil setting.
Cottage in Martinsburg
4.97 out of 5 average rating, 472 reviews

Last Rodeo Cottage

Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.

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