Vacation rentals in Middleway

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

Architectural Mountaintop Retreat | Shenandoah

Perched on a secluded 30-acre ridge, this quiet sanctuary shaped by light offers warm wood, panoramic windows, and calm modern comfort. Two spacious living rooms, a sunlit reading loft, and serene bedrooms create space to gather or drift into solitude. Wander private hiking trails, unwind by the fire pits, and take in sweeping Blue Ridge views - quietly above it all. A place where groups and families gather without noise and where every corner invites you to slow down and breathe more deeply.

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.

Cedar Hill Cottage- 3 mi to I-81 & Rt 11

Cozy, pet-friendly home on a quiet road near Winchester, Va (about 7 miles outside of the center of Winchester). Enjoy peaceful surroundings, a large porch, and a spacious yard to relax or let your pets play. Conveniently located close to shopping, restaurants, I-81, and Rt 11- the perfect blend of comfort, charm, and convenience for your stay. There is a shopping center 5 minutes away from the house. Downtown Winchester is 7 miles away & about 10-15 min drive depending where you are going.

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.

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.

Ranson Retreat | Sleeps 5-6 + Free Parking

Relax in this spacious, modern 3-bedroom (4beds), 2.5-bath home designed for comfort and convenience. This home is perfect for families or small groups. Enjoy a fully equipped kitchen, cozy living space, self check-in, WFH desk with fast wifi. 24/7 Responsive host available if needed. Conveniently located minutes local wineries, dining, casino, historic landmarks, and major roadways. Quiet, clean, and comfortable—your home away from home awaits! Ask us about extended stay discounts!

Historic Charles Town- Artist's Home

In historic downtown Charles Town, this relaxing home is a perfect get away and also close to many local attractions. Walk to restaurants, coffee shops, and boutiques. In a quiet neighborhood, 5 blocks from the charming downtown, this welcoming older house has historic details, charming artsy decor, covered front porch, covered back porch, and large fenced yard. One of the 4 bedrooms is on the 1st floor. 8 mins to historic Harpers Ferry, 12 mins to Shepherdstown shops and theater.

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.

Relaxing Getaway Near Shenandoah River Access

Come and enjoy our spacious 3bd/2ba home in Harpers Ferry, WV just across the Virginia state line and close to many local attractions! Perfect for families featuring a large fenced in backyard. Centrally located within 15 mins from historic Harpers Ferry; within 1/2 mile of public boat access to the Shenandoah River; 2 miles to Appalachian Trail; less than 15mins to numerous breweries & wineries; 10mins to Charles Town Casino. Enjoy all this wonderful area has to offer!

The Serenity in DT Charles Town near Harpers Ferry

Welcome to our 1 bedroom basement apt in the charming, historic town of Charles Town, West Virginia! Nestled in the scenic beauty of the Shenandoah Valley, this delightful property offers a perfect blend of comfort, convenience, and a touch of old-world charm. Whether you're visiting for a weekend getaway, exploring the area's rich history, or attending one of the nearby events, our Airbnb is an ideal home base for your adventures.

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.