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

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

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

4.87 out of 5 average rating, 767 reviews

Top guest favorite

The modern ranch home features a two-story design with a wide front staircase leading to the upper porch. The exterior is painted in neutral tones and is surrounded by green grass and trees, with a clear blue sky visible overhead.

Home in Winchester

Swim, kayak, fish, and enjoy nature on Back Creek

Classic Georgian home in the Shenandoah Valley with cherry wood floors and french chandeliers. Six acres of pristine, waterfront privacy just 20 minutes from downtown Winchester. There are 3 bedrooms (1 king bed and 2 queen beds) and 3 bathrooms. Upstairs, there is an open-concept living area with a full kitchen, pantry and laundry room. Downstairs, there is a regulation pool table, dart board, reclining sofa, and workspace with PC and printer. The front porch has a sweeping view of Back Creek.

4.94 out of 5 average rating, 65 reviews

Superhost

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

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

4.92 out of 5 average rating, 207 reviews

Top guest favorite

A cozy living area features a stone fireplace as a focal point, surrounded by comfortable seating options including a brown sofa and floral-patterned armchair. A wooden coffee table sits in the center, complemented by a rocking chair and natural light coming through two windows.

Guest suite in Clear Brook

Bluebird Bungalow

Tucked neatly into a cul-de-sac on 6 acres ; spacious yet cozy; this is an inviting place to visit. Its private, garden-graced entrance hints at the pleasing interior. The butcher block counters and up to date appliances make the kitchen a joy to work in. A desk with charging area and reliable fast internet is found in the living area. The bedroom/bath/closet suite is comfortable with ample storage for an extended stay. Convenient, lighted parking is available only a few feet from the door.

4.97 out of 5 average rating, 76 reviews

Top guest favorite

The exterior of the cabin is showcased, featuring large vaulted windows that allow natural light to fill the space. The deck is furnished with a table and chairs, surrounded by a lush yard and trees displaying autumn colors.

Cabin in Gerrardstown

The Nest: Modern Cabin Retreat on 5 Wooded Acres

Welcome to The Nest, a light‑filled, chalet‑style cabin tucked into 5 wooded acres. A short drive from Berkeley Springs, Harpers Ferry, and Cacapon State Park, it’s your base for hot springs, hiking, trails, and small‑town restaurants. By day, explore paths, wineries, and historic main streets. By night, come “home” to star‑studded skies, mountain views, and wildlife. With fast Wi‑Fi, a workspace, and a fully stocked kitchen, The Nest is perfect for families, couples, and remote workers.

4.98 out of 5 average rating, 211 reviews

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

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.

4.97 out of 5 average rating, 136 reviews

Guest favorite

The front porch features two white rocking chairs with red cushions, positioned next to a welcoming red door adorned with a wreath. Lush flowers bloom in a garden bed below, adding color to the inviting entrance.

Home in Winchester

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

4.97 out of 5 average rating, 294 reviews

Top guest favorite

Home in Inwood

Farm-Lane Retreat w/ Game Room • 1 Min to I-81

Peaceful Farm Retreat with Mountain Views, Game Room & Fire Pit Escape to the quiet countryside in this spacious 3-bedroom, 3-bath farmhouse tucked away on a farm lane. Surrounded by rolling hay fields and framed by stunning views of North Mountain, this home offers the perfect blend of privacy, comfort & open-space. Inside, you’ll find three cozy bedrooms plus bonus beds in the finished basement—plenty of space for families or groups. The highlight of the home is the game room.

5.0 out of 5 average rating, 37 reviews

Top guest favorite

An open living area features hardwood floors and a comfortably arranged seating set, including a sofa and a lounge chair. A modern kitchen with sleek cabinetry and stainless steel appliances is visible, alongside a dining area with a small table. Natural light fills the space.

Condo in Charles Town

Upscale Walkup in Downtown Charles Town

This professionally designed 1 bedroom apartment in downtown Charles Town- walking distance to cafes, restaurants, and landmarks, and also close to all there is to do in the Historic Harpers Ferry, Virginia Wine Country, and Shenandoah River rafting. This is a full 1-bedroom apartment with an additional sofabed. This 3rd-level walk-up with hardwood floors, a fully stocked kitchen, open to the family room with a pull-out couch and TV (with Roku). Also, a small separate office.

5.0 out of 5 average rating, 40 reviews

Top guest favorite

Home in Clear Brook

Sunrise/Sunset Views

Enjoy the Sunrise and beautiful Sunsets from this House on a hill. Located on a tranquil farm in Clear Brook, VA. Surrounded by nature in a peaceful, quiet setting. Celebrate days end while experiencing a glorious Sunset and stargazing from the spacious deck or fire pit. Perfect location in the country but close to downtown Winchester, VA. Visit Washington, DC or go tubing in Harpers Ferry, WV. Local Wineries and Breweries nearby. No pets- this is a working farm.

5.0 out of 5 average rating, 13 reviews

Guest favorite

An inviting entryway showcases a wooden staircase leading to a loft area. The walls are adorned with wooden paneling and a prominent 'Station' sign. A coffee station and laundry area are conveniently positioned on one side, enhancing functionality.

Vacation home in Martinsburg

The Train Station Lodge

The Train Station Lodge is a one-of-a-kind guest house on 7 wooded acres in Martinsburg, WV. Inspired by the area’s railroad history, it offers private walking trails, peaceful forest views, custom character, and a memorable stay unlike a standard rental. Relax in the oversized antique cast iron tub, enjoy the unique train-themed design, and explore nearby Harpers Ferry, Shenandoah, and other local attractions.

4.95 out of 5 average rating, 112 reviews

Top guest favorite

A modern kitchen features sleek cabinetry and a stainless steel stove. A vibrant green wall with an illuminated neon artwork adds a pop of color. A dining table with metal chairs is positioned against the wall, creating a stylish yet functional space.

Home in Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown!

Eclectic space full of little treasures I’ve picked up during my travels. You will find the place cozy enough for a reset and recharge weekend but also inspiring for gatherings and celebrations. Take advantage of the books, games and excellent SONOS system in the house as well as outside on the patio. This place is great for music lovers and people who enjoy a change from the ordinary.

4.93 out of 5 average rating, 784 reviews