Vacation rentals in Middletown

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...

Farm Stay in a luxury tiny home with hot tub

Welcome to “Horsefeathers” a tiny home on an historic property where you will be immersed in a farm experience! Although tiny, this house is equipped with all top of the line luxuries to include a personal hot tub, an automatic cappuccino maker, a king nectar mattress-just to name a few. Only minutes to Winchester the location is convenient to restaurants and shopping yet you’ll feel like you have been transported back in time to a working homestead where you can interact with all the animals.

Cozy Reliance Retreat with Beautiful Views

Welcome to the Reliance Retreat in the heart of the Shenandoah Valley! Our luxurious space is inviting and tranquil. Whether you're just passing through or need some peace and quiet away from the city, this cozy house has an amazing mountain view we know you'll enjoy. The house sleeps two and includes all the amenities you'll need in every area of the home. We hope you'll grab a book, your favorite snacks and find yourself a cozy spot whether it's inside, on the patio, or out by the fire pit

The Sanctuary in the Shenandoah Valley

Rest and unwind with your family or friends at the Sanctuary. We designed this space with gathering and connection in mind. Enjoy natural lighting and open concept living in our newly renovated 19th century church building. Meals can be prepared in the spacious kitchen and enjoyed together around a 12-foot farmhouse table. After meals transition to our spacious yet cozy living room. If you don't want to stay in, explore the Shenandoah Valley's great outdoors, rich history, and fine dining.

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. An inviting front porch with swing is waiting for you @walnuthillcabin

The Vale at Será - modern w/plunge pool + sauna

Escape to a modern cabin tucked into 12.5 acres of private forest in Wardensville, WV, just two hours from DC. Thoughtfully designed to bring the outdoors in, Será at Sandy Ridge is an architect-husband and wife designed and owned nature stay that blends elevated simplicity with deep comfort. The Vale features expansive views, chef’s kitchen, spa-like bathrooms, wood burning stove, and a private heated plunge pool/hot tub, and is stocked with thoughtful amenities for you and yours.

Dog Friendly Mountain Retreat w/ Views & Firepit

Welcome to our Winchester Retreat! ✅ Panoramic Views ✅ Fire pit Area ✅ Relaxation Come relax at our 3-bedroom home offering a perfect escape with breathtaking views of the Shenandoah Valley. Relax in the living area, featuring two big picture windows that frame the Shenandoah Mountains. Located just a short drive from Washington, DC, and about 30 min from the Shenandoah park entrance, our home is an ideal getaway for both relaxation and exploration.

Cabin With Wood Burning Hot Tub

Escape to our modern cabin on 12 private acres. Unwind in the wood-burning hot tub, embracing the surroundings and stars at night. With a contemporary design and natural light, this retreat blends with nature. Explore private trails throughout the property, enjoying nature and the fresh air. Inside, find comfort in the fully equipped kitchen and cozy living area. Perfect for a peaceful getaway, our secluded home provides privacy and relaxation.

Skyview Farmhouse

Relax with the whole family at this peaceful place to stay. Great views, surrounded by 3 wineries, 5 farm markets and 3 wedding venues. You will be next door to Orchard View Farm Events, 1 mile from West Oaks wedding event center, 5 miles from Oakdale Farm wedding Venue, and 30 minutes Shenandoah’s National Forest etc. please let me know how many guests are coming. There is a washer and dryer to use upon request. We can’t wait to be your host!

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.

Mountaintop Retreat with Wood Fired Hot Tub

Doah House is a private retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. A calm container for rest and observation, the pace softens, shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing the light, the air, the sound. Each day feels different. The forest shifts, and you might, too.

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit

Hidden in the Valley sits on 30 private, wooded acres adjoining the George Washington National Forest. This remote property offers a pool, fire pit and foot trails throughout, perfect for your furry companions! If you’re looking for a true escape to nature, surrounded by Virginia’s best hiking trails, wildlife and clear, starry night skies, Hidden in the Valley is the getaway for you!