Vacation rentals in Middleway

Creekside Pine Retreat

Escape to a serene two-acre retreat in a lush West Virginia pine forest. This modern, family-friendly home offers creek access stocked with trout and bass, and a cozy fire pit for evening gatherings. Enjoy both seclusion and proximity to top attractions: Summit Point Motorsports Park (15 mins), Hollywood Casino (20 mins), and Harpers Ferry and Shepherdstown (30 mins). Perfect for guests seeking comfort, adventure, and relaxation. Basement arcade/game room and RV parking available w/50 Amp hookup

Spectacular View, PET FREE, Skylight and Hot Tub

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 peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, "Mind Blowing" 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

Stone House Mansion (1757)- Basement Apartment

Immerse yourself in history as our guest at Stone House Mansion, listed on the National Register of Historic Places. Home to Revolutionary War, French & Indian War, & War of 1812 officers, statesmen, and Congressmen. Near historic Shepherdstown, Harpers Ferry, & Antietam National Battlefield. The apartment has everything you will need for a comfortable stay. The private basement level apartment is ideal for couples, families, solo adventurers, & business travelers (available for extended stay).

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

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 new 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, well lit parking is available only a few feet from the entrance.

Quaint Work-Play Space

Enjoy all the amenities of home on a smaller scale in this fully furnished, private upstairs suite equipped with living room, bedroom, full kitchen and bath. Come and stay for short term work OR come to play in an area rich with history, antique shops and outdoor adventure. Guests will have private entrance with numeric lock pad. Security through Ring cameras. All codes will provided prior to arrival. There are stairs- upstairs unit and laundry room. No handicap access.

The Big Room - Historic Schoolhouse

Checkout as late as 8pm on Sundays! Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. The Railside Market serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia.

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.

The Nashville

Experience the vibrant pulse of downtown Martinsburg at The Nashville Airbnb. This private apartment features a spacious bedroom with a queen-size bed and TV. The family room boasts a 75" TV and is thoughtfully designed to showcase the artistic and downtown style reminiscent of Nashville, TN. This second story apartment is amazing! Conveniently located within walking distance to the Marc Train, Bars, Restaurants, and Shopping.

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.

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.

Studio 203

Chic and modern, this downtown apartment is the perfect spot for a night out in the city. It features high ceilings, elegant furniture, and a spacious luxury bathroom. You'll love the stunning views of Queen Street from the large picture window. Be prepared for some stairs and the usual urban noise from nearby apartments.