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...

The Bird's Nest - Cabin by the River

Located on one of the Seven Bends of the Shenandoah River, the Bird’s Nest is a brand new, custom built 800 square foot cabin featuring an open loft with king bed and skylights, steam shower, heated bathroom floor, and gas fireplace. Exterior amenities include a hot tub, gas grill, gas fire pit table, fire pit by the river, and private river access in a peaceful, wooded setting. Kayaks/tubes are available to use to float down the river with the unique ability to park/exit on the hosts’ property.

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.

Horizon | Hot/Cold Tub, Fireplaces, Sauna, EV Plug

The Horizon cabin at Arête, your luxury 2 BR mountain A-frame retreat with breathtaking views. Enjoy a private two-level deck with a hot tub, cold plunge, and cedar steam sauna for ultimate relaxation. Inside, the spa-inspired bathroom offers heated floors & towel rack, and a soothing shower with five massaging heads. The kitchen is fully equipped, and you can enjoy al fresco dining using the outdoor Napoleon grill. Relax by the indoor wood fireplace or outdoor fire pit (firewood provided).

Brewhouse renovated row house steps from downtown

Situated in the heart of downtown Winchester, you'll be within walking distance of a vibrant brewery, delicious restaurants and local culture. The Brewhouse is a perfect blend of modern comfort and original architecture. Incredible care has been taken to create a vintage space and a real haven for beer lovers! Whether you are visiting for business or pleasure you will love this one of a kind spot and we look forward to ensuring that your stay is nothing short of exceptional !

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.

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.

Starlight Farmhouse | Dog-Friendly + Mountain View

Starlight Farmhouse is a dog-friendly escape with a large fenced yard, sweeping farm-and-mountain views, and some of the darkest skies in the Shenandoah Valley. One of the valley's original farmhouses, it pairs real history with everyday comfort. Unwind by the fire pit, sway in the hammock, or catch the sunset from the porch — with hiking, ATV trails, and Skyline Drive close by, and Luray Caverns an easy day trip.

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!