Holiday 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...

The Cottage at the Barb Farm

The Cottage at the Barb Farm is a cozy two story cottage nestled in the Shenandoah Valley on the historic Fisher's Hill Battlefield. The cottage was used as the summer kitchen in the civil war days. It was rebuilt in 1991 to the current cottage. There is lots of civil war history to discover, hiking trails, wineries, and breweries in the area. The town of Strasburg is about 15 minutes away. If you're looking for a weekend getaway or a relaxing vacation in the mountains, this is the perfect spot!

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.

Mint House Cottage

Mountain views from living areas and westerly facing private deck where you can enjoy sunsets over the mountains. C lose to hiking, caverns, Skyline Drive, Shenandoah and GW National Parks. Many hiking trails, from Fox Hollow to Signal Knob. Peaceful setting with walking paths around fields, or through the woods, catch and release fishing in four-acre pond all on historical Quaker farm. High speed internet. Kid and Pet friendly Any specific needs, let me know I will try to accommodate them.

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.

Cedar Creek Wayside Castle

1930 Stone House 'Mini Castle' on 9 private acres near Strasburg Virginia bordering Cedar Creek Battlefield and Belle Grove Plantation National Park. Home was built by Otis Elevator company in 1930 for their daughter. You have nature trails and fire pit, swimming pool (opened April 15th), deer and wildlife too. Short walk to historic Ceder Creek. Full estate is yours to play and relax. No dogs in pool. Pool is open early April to early October usually. Hot tub is ready year round.

Cozy 3BR Retreat w/ Patio, Fire Pit & Yard

Your cozy home away from home in Winchester! Whether you're visiting family, working nearby, exploring the Shenandoah Valley, or just looking for a relaxing getaway, this bright and welcoming home is the perfect place to unwind. Enjoy comfortable bedrooms, a fully equipped kitchen, fast WiFi, a spacious backyard with a large patio, and all the comforts of home—all in a quiet neighborhood just minutes from shopping, dining, wineries, hiking, and Old Town Winchester.

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!

The Happy Farmhouse

Come take a break and stay at our charming farmhouse, where you can breathe in the crisp morning air, watch the butterflies, and slow down for a while. The Happy Hen Famhouse has 3 bedrooms, 2 full bathrooms, and a fully-stocked kitchen. Enjoy sitting on the porch, relaxing in the hammock, playing lawn games, or making s’mores by the fire pit. Enjoy a peaceful retreat while still being near shopping, wineries, farm markets, and restaurants!

Windy Knoll Adventure | River Front | Hot Tub!

Discover our Black Modern Charm Home, a private retreat atop 35 acres with sweeping mountain and Shenandoah River views. Relax in the hot tub overlooking the river, fish or kayak below, and unwind by the campfire in this peaceful woodland setting. 🌲♨️ Designed for comfort and escape, this modern retreat is perfect for unplugging, reconnecting, and enjoying nature at its finest. Book now for a true mountaintop getaway. ✨

Aunt Tim's Farmhouse

Our farmhouse is located approximately 5 miles west of Historic Winchester, VA. The house is situated on 106 acres of an operational farm. You may see family members and friends tending honey bee hives, working in the detached garage, gardening, and completing other farm chores. The house is solely occupied by our guests. Come on out to enjoy some peace and quiet and take advantage of all Mother Nature has to offer!