Vacation rentals in Stephens City

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Top-rated vacation rentals in Stephens City

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Superhost
An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.
Cottage in Winchester
4.99 out of 5 average rating, 490 reviews

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...

Top guest favorite
Tiny home in Stephens City
5.0 out of 5 average rating, 159 reviews

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.

Top guest favorite
An open concept living area features a spacious kitchen with a large island and dining space, complemented by a farmhouse table. Natural wood flooring and large windows introducing soft light contribute to a warm environment. A Christmas tree adds a festive touch in the corner.
Religious building in Stephens City
4.96 out of 5 average rating, 136 reviews

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.

Top guest favorite
A cozy corner features a cushioned armchair adorned with decorative pillows, next to a small dark wood table with a lamp. A decorative bookshelf holds various books, with warm sunlight illuminating the space. A wooden staircase leads to the upper level.
Home in Winchester
4.98 out of 5 average rating, 224 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Guest favorite
The exterior of a charming house is shown, featuring a white façade with a unique architectural detail at the roofline. A welcoming, wheelchair-accessible ramp leads to the front door, surrounded by manicured shrubs and a green lawn with open fields in the background.
Home in Middletown
4.9 out of 5 average rating, 153 reviews

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

Top guest favorite
A spacious dining area features a wooden table with woven placemats, surrounded by upholstered chairs. Natural light fills the room through the windows. A comfortable seating arrangement with a sofa is visible in the background, complemented by a television on a console.
Apartment in Winchester
4.97 out of 5 average rating, 358 reviews

Downtowner

No hassle parking on premises and a private entrance. The "Downtowner" is a 1920's era restored home in a quiet residential section of Winchester's Historic District and just a short stroll to the downtown "pedestrian only" walking mall with restaurants, cafes, and shops. Clean and spacious, the apartment is complete with bed linens, towels, etc. and stocked with water in the fridge as well as a Keurig with coffee options, tea, hot chocolate, etc...Xfinity HDTV with voice remote control.

Top guest favorite
A spacious bedroom is furnished with a large bed covered in a crisp white duvet. Two bedside lamps flank the bed on dark wood nightstands. Natural light enters through a window, and neutral gray walls complement the cozy atmosphere.
Home in Winchester
4.98 out of 5 average rating, 248 reviews

Colonial Getaway Near Old Town Historic Winchester

Colonial style home- enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms and 2.5 bathrooms. Perfect for a family or a longer stay. Just a few miles drive to Old Town Winchester which includes numerous restaurants, bars, shopping and some kind of event... like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. Near by to other scenic attractions as well- Shenandoah National Park, Luray Caverns, and Harper's Ferry!

Guest favorite
Loft in Winchester
4.74 out of 5 average rating, 737 reviews

Immerse yourself in Old Town Winchester (Apt #4)

Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops, and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky, and awesome, we are your place!

Superhost
A cozy sitting area is illustrated with two floral paintings on light green walls. A beige sofa is adorned with colorful pillows in shades of orange and green. A sleek black lamp is positioned beside the sofa, providing focused lighting, while a small table holds decorative items.
Apartment in Stephens City
4.92 out of 5 average rating, 12 reviews

Newtown Cozy Cottage Basement

Keep it simple at this peaceful and centrally-located brand new apartment. Enjoy a walk or run in the quiet neighborhood. Minutes away from Rt.11, Rt. 81 and Rt. 37. Also minutes from shops, delicious restaurants, wineries, and one of the few remaining drive-in movie theaters in the country. Historic downtown Winchester is only minutes away. Nearby national parks and historic sites offer endless possibilities. Take a day trip to DC- less than 2 hours away.

Top guest favorite
A cozy living area features a red sofa adorned with decorative pillows, facing a wooden media console with a television. A round coffee table sits centrally on a patterned rug. Two lamps provide soft lighting, creating an inviting space for relaxation.
Apartment in Stephens City
5.0 out of 5 average rating, 22 reviews

Spacious Charming Basement Apt

This newly renovated space with private entrance is perfect for traveling professionals and vacation travelers alike. Close proximity to shopping and restaurants. Just off Main St (Rt 11), it is convenient to Rts 37 and 81. Less than 15 minute drive to Winchester Medical Center, Shenandoah University. Visit Local Wineries/Family Drive In Theater/ Harpers Ferry/ Skyline Drive/ Historic Winchester/ Take a day trip to DC- just 1.5 hours away. Options abound!

Superhost
A serene landscape is depicted, showcasing a vibrant sunset over fields and distant trees. The horizon is illuminated with warm hues, and a calm atmosphere is suggested by the expansive farmland extending into the distance.
Home in Winchester
4.98 out of 5 average rating, 57 reviews

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!

Guest favorite
The exterior of the townhouse features two large windows on the upper floor, a welcoming front door framed by a porch. A small patio area is furnished with a bistro table and two chairs, surrounded by neatly arranged landscaping and stone pathways.
Townhouse in Winchester
4.93 out of 5 average rating, 314 reviews

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.

Popular amenities for Stephens City vacation rentals