Vacation rentals in Stephens City

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Top-rated vacation rentals in Stephens City

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Top guest favorite
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

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...

LocationValueAccuracy

4.99 out of 5 average rating, 496 reviews
Top guest favorite
Tiny home in Stephens City

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.

FamilyValueLaundry

5.0 out of 5 average rating, 172 reviews
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

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.

FamilyValueCondition

4.96 out of 5 average rating, 136 reviews
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

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 !

LocationFamilyIndoor spaces

4.98 out of 5 average rating, 225 reviews
Superhost
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

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

FamilyLocationDecor

4.9 out of 5 average rating, 157 reviews
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

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.

FamilyLocationOutdoor spaces

4.97 out of 5 average rating, 359 reviews
Guest favorite
Loft in Winchester

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!

LocationFamilyCondition

4.74 out of 5 average rating, 740 reviews
Guest favorite
The front porch features two white rocking chairs with red cushions, positioned next to a welcoming red door adorned with a wreath. Lush flowers bloom in a garden bed below, adding color to the inviting entrance.
Home in Winchester

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

LocationValueComfort

4.97 out of 5 average rating, 294 reviews
Top guest favorite
An inviting living area features a brick accent wall with a mounted flat-screen TV above a rustic fireplace. A collection of spice jars is displayed on a wooden shelf, adding a touch of charm. A cozy cowhide rug lies on the hardwood floor, enhancing the space.
Townhouse in Winchester

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 !

LocationFamilyKitchen

4.95 out of 5 average rating, 109 reviews
Guest favorite
A classic A-frame cabin is surrounded by trees, featuring a spacious deck with comfortable lounge seating. Soft lighting accentuates the inviting outdoor space, while large glass doors provide a glimpse into the cozy interior. The modern roof complements the rustic wooden facade.
Cabin in Front Royal

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

LocationFamilyQuiet

4.95 out of 5 average rating, 319 reviews
Guest favorite
Home in Winchester

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.

LocationFamilySleep quality

4.9 out of 5 average rating, 30 reviews
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

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.

ValueLocationCheck-in

4.93 out of 5 average rating, 14 reviews

Popular amenities for Stephens City vacation rentals