Vacation rentals in Middleway

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Top-rated vacation rentals in Middleway

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

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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, 470 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 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, 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.

Top guest favorite

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, 104 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.

Guest favorite

Home in Harpers Ferry

4.93 out of 5 average rating, 192 reviews

Cozy Tiny House in Harpers Ferry Tub & River Views

Pet Free, 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 peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

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, 471 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.

Guest favorite

The cottage features a welcoming exterior with a mix of orange and cream siding. Large windows allow natural light to fill the interior, while the front porch provides a shaded entry. A landscaped yard with trimmed shrubs surrounds the home, set against a backdrop of bare trees.

Cottage in Leesburg

4.93 out of 5 average rating, 286 reviews

The Cottage at Stone Tower Winery

The Cottage at Stone Tower Winery is a fully renovated, one-bedroom house located only an hour from DC, 30 minutes from Dulles Airport, and 15 minutes from Leesburg. The home is perfectly situated to enjoy a peaceful stay in the country and serves as an ideal location to explore the Northern Virginia wine region and historic Loudoun County.

Superhost

A spacious bedroom is illuminated by natural light from two large windows. A comfortable bed is styled with soft linens and a warm blanket. Two armchairs sit invitingly in the corner, and textured rugs decorate the hardwood floor.

Apartment in Charles Town

4.8 out of 5 average rating, 110 reviews

Spacious apt with King beds in DT Charles Town

Welcome to our charming 2-bedroom Airbnb in downtown Charles Town, WV! This modern retreat offers two spacious bedrooms with king-size beds for a comfortable stay. Explore the city's attractions and enjoy a cozy night's sleep in stylish accommodations. Book now for a memorable stay in the heart of Charles Town!

Guest favorite

A modern retreat is nestled among tall trees, featuring expansive glass walls that provide unobstructed views of the surrounding woods. The structure is elevated on a platform, showcasing natural wood accents that blend harmoniously with the environment.

Vacation home in Fort Valley

4.97 out of 5 average rating, 120 reviews

New Modern Glass Retreat Mountain View

Enjoy the sights and sounds of George Washington National Forest when you stay in this beautiful, new and unique place. Set on over 6 acres right in the George Washington National Forest. There is a second Retreat on site called Forest View Glass Retreat. Try that Glass retreat if this one is booked. 😊

Guest favorite

A single-story home is surrounded by a lush green lawn, with a blooming pink tree to the left and another tree on the right. The front entrance features steps leading to a dark door, flanked by windows. Light snow covers the ground, contrasting with vibrant foliage.

Home in Inwood

4.95 out of 5 average rating, 545 reviews

The Inwood House- easy on/off I-81

Perfectly situated 1 mile off of I-81 in The Eastern Panhandle of WV. Completely renovated interior has been designed to be easily accessible. Enjoy this 2 bedroom home on 1 acre all to yourself. Near restaurants and grocery store. Light continental breakfast included.

Top guest favorite

A cozy studio apartment is featured, with a queen bed positioned near a window draped in light curtains. An open kitchen area displays wooden cabinetry and modern appliances. A small dining table with two stools is adjacent to the kitchen, while a television is visible across from the bed.

Farm stay in Shenandoah Junction

4.94 out of 5 average rating, 198 reviews

Historic Rockdale Private Studio Apartment

Private cozy studio apartment. Sunny porch. Custom kitchen. Bathroom with heated floor and huge shower with two shower heads. Full sized Washer and Dryer. Starlink internet. Roku Smart TV in unit. On 24 acre tree farm with sweet GOATS, wildlife, and walking paths.

Top guest favorite

The unique dome structure is surrounded by lush trees, featuring large windows and a cozy entrance. An inviting outdoor seating area with a fire pit and black chairs is positioned on the wraparound deck, accompanied by a hammock and a hot tub.

Dome in Mercersburg

4.99 out of 5 average rating, 238 reviews

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

Escape to this architectural marvel where luxury meets nature, just minutes from Whitetail Resort. Wake up in your king-sized sanctuary as sunlight floods the open concept living space through panoramic windows.

Guest favorite