Holiday houses in Kernstown

4.99 out of 5 average rating, 496 reviews

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...

FamilyValueBackyard

4.91 out of 5 average rating, 424 reviews

A contemporary building with a mix of stone and modern gray walls is showcased, featuring large glass windows and wooden accents. A bright yellow door provides a pop of color at the entrance. The surrounding area includes wooden railings and landscaped greenery.

Apartment in Winchester

Old Town 1920s Gas Station with Hot Tub

1920s Refurbished Gas Station with hot tub repurposed into a beautiful luxury apartment. Private parking/EV charging, private hot tub, full kitchen, custom rain shower, high speed wifi and smart TV. There is plenty of light with frosted garaged doors, all modern appliances, laundry and coffee nook in an open living design. Be a part of Old Town Winchester in this unique getaway, walking distance to shops, downtown eateries and our neighborhood Pizzoco Pizza Parlor one block away. Pets welcome!

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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.

ValueLocationLong stay

5.0 out of 5 average rating, 172 reviews

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.

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 !

ValueFamilyKitchen

4.97 out of 5 average rating, 359 reviews

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.

ValueLocationDecor

4.74 out of 5 average rating, 740 reviews

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!

ValueFamilyAccuracy

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.

4.97 out of 5 average rating, 294 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.

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Superhost

Place to stay in Winchester

Secret Gardens Carriage House

Nestled within the city of Winchester, Va. in the Shenandoah Valley, 30 minutes from the Blue Ridge Mountains and a 5 minute drive to the Old Town Walking Mall, sits this charming carriage/guesthouse on 2+ secluded acres. The Carriage House dates from the 1920’s and features a bedroom with an antique four-poster bed, full bathroom with old-fashioned pedestal tub and shower, beautifully updated kitchen, a private screened-in porch with a gorgeous view of Zen Gardens and much more!

ValueLocationLong stay

4.86 out of 5 average rating, 95 reviews

4.95 out of 5 average rating, 109 reviews

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 !

FamilyValueBackyard

4.95 out of 5 average rating, 319 reviews

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!

FamilyValueBiking

4.9 out of 5 average rating, 30 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.

LocationFamilyCleanliness

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.