
Vacation rentals in Stephens City
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Stephens City
Guests agree: these stays are highly rated for location, cleanliness, and more.

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
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
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
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
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
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
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
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
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
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
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
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 reviewsPopular amenities for Stephens City vacation rentals
Other great vacation rentals in Stephens City

Spacious Charming Basement Apt
LocationComfortGetting around
5.0 out of 5 average rating, 22 reviews
Springdale Mill Farmhouse with Spa House
ValueFamilyHospitality
4.87 out of 5 average rating, 93 reviews
Dog Friendly Mountain Retreat w/ Views & Firepit
ValueLocationComfort
4.83 out of 5 average rating, 52 reviews
Queen of Winchester - Three Bedroom Apartment
ValueLocationGetting around
4.75 out of 5 average rating, 71 reviews
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
ValueLocationAccuracy
5.0 out of 5 average rating, 19 reviews
Epic View*Hot Tub*Fire Pit*Pet Friendly
LocationValueGetting around
4.89 out of 5 average rating, 44 reviews
Merrimans Hope 5BR spacious & stunning on 2 +acre
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 7 reviews
"Shenandoah View"
ValueFamilyAmenities
4.97 out of 5 average rating, 33 reviewsDestinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Ocean City Vacation rentals
- Pittsburgh Vacation rentals
- Columbus Vacation rentals
- Cleveland Vacation rentals
- Virginia Beach Vacation rentals
- Niagara Falls Vacation rentals
- Raleigh Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Shenandoah National Park
- Luray Caverns
- Bryce Resort
- Berkeley Springs State Park
- Harpers Ferry National Historical Park
- Rock Gap State Park
- South Mountain State Park
- Cacapon Resort State Park
- Shenandoah River Outfitters
- Sky Meadows State Park
- Greenbrier State Park
- Prince Michel Winery
- Green Ridge State Forest
- Reston Town Center
- Jiffy Lube Live
- Bluemont Vineyard
- Antietam National Battlefield
- Weinberg Center for the Arts
- Dulles Town Center
- Skyline Caverns
- Gambrill State Park
- Old Town Winchester Walking Mall
- Big Cork Vineyards
- Whitetail Resort





