Holiday houses in Gerrardstown

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Top-rated holiday rentals in Gerrardstown

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Superhost
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.
Tiny home in Harpers Ferry
4.96 out of 5 average rating, 159 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.

Guest favourite
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, 693 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 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
4.95 out of 5 average rating, 171 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
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, 374 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, 179 reviews

The Nest: Cozy Chalet - Wi-Fi, Deck and Grill

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.

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, 108 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 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
4.93 out of 5 average rating, 273 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
4.94 out of 5 average rating, 126 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 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, 235 reviews

Modern Eclectic Treetop Cabin With Hottub

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.

Top Guest favourite
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.
Home in Winchester
4.97 out of 5 average rating, 236 reviews

Full basement with private entrance. Hot tub

Cozy movie themed basement is exactly what you are looking for. Classic AirBnB-we are opening our house to you! Space is completely private. Bedroom with queen bed. High speed internet. Private bath w/shower. Small refrigerator, microwave, 2 flat screen TVs table and chairs and multiple couches in a large family room w/Sofa bed. 1000 square feet of space! Home 2 miles outside of the city of Winchester in Frederick County.

Top Guest favourite
A charming stone cottage with a wooden front porch features a sloped roof and a brick chimney. Surrounded by trees, the cottage is set on a grassy area, providing a sense of seclusion. Large windows and a welcoming entrance enhance the exterior appeal.
Cottage in Winchester
4.98 out of 5 average rating, 530 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.

Top Guest favourite
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
4.95 out of 5 average rating, 503 reviews

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 Gerrardstown holiday rentals