Vacation rentals in Stephenson

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Top-rated vacation rentals in Stephenson

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Superhost

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

4.9 out of 5 average rating, 364 reviews

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!

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, 205 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 !

Top guest favorite

Aerial view captures the historic downtown Winchester at sunset, with buildings showcasing varied architectural styles. The warm glow of the sun illuminates the skyline, highlighting the rooftops and the distinctive features of the surroundings. Streets lined with trees provide a scenic backdrop.

Apartment in Winchester

4.89 out of 5 average rating, 237 reviews

Downtown FUN! Personal Mid Century 2bd Apartment!

Welcome to Blossom! Your own, private pied-à-terre, located in Winchester's historic district, 1 block from the Old Town Walking Mall! Blossom's UBER-LUX upgrades include a fully-stocked custom kitchen, marble countertops, new stainless steel appliances, high speed internet, gleaming hardwood floors, queen size canopy beds, heavenly memory foam mattresses, 50' smart TV, all delivered with a Euro MCM flare! Blossom is ideal for a romantic getaway, smart business travel, or a quick City escape!

Top guest favorite

A comfortable seating area features a gray sofa positioned against exposed brick walls. A tan upholstered bench serves as a coffee table in front of the couch, while a light accent lamp provides illumination. Hardwood floors add warmth to the space.

Apartment in Winchester

5 out of 5 average rating, 223 reviews

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

Top guest favorite

A cozy living area features two light brown sofas adorned with colorful throw pillows. A glass-top coffee table is centered between them. Sunlight filters through the large windows, which are framed by light-colored curtains, creating a bright and inviting space.

Apartment in Winchester

4.97 out of 5 average rating, 299 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 living area features vaulted ceilings with large windows allowing natural light to fill the room. A comfortable sofa faces a central coffee table, with a dining area containing a round table and chairs nearby. Shelving units display books and decorative items, enhancing the inviting space.

Cabin in Gerrardstown

4.98 out of 5 average rating, 167 reviews

The Nest: Cozy Chalet w/Wi-Fi, Deck & Grill

The Nest is a chalet-style cabin tucked into the tree-lined mountains of Berkeley County, WV. It offers adventure, a quiet retreat & good family fun. With 5-acres in the countryside, you'll enjoy star studded skies on clear nights & wake up to birds singing & deer wandering, with mountain views through vaulted windows. The Nest is near Martinsburg, Berkeley Springs, Harpers Ferry, Shepherdstown, Charles Town & Cacapon State Park, among other go-to destinations on the Eastern Panhandle.

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

4.97 out of 5 average rating, 211 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!

Superhost

The loft apartment features rich burgundy walls, a cozy seating area with a green couch, and a wooden dining table. A small kitchen is visible, along with a staircase leading to an upper level. Natural light floods through large windows, highlighting the inviting atmosphere.

Loft in Winchester

4.72 out of 5 average rating, 674 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!

Guest favorite

A historic home is positioned on a tree-lined street, featuring a charming façade with a welcoming entrance. Vibrant flowers adorn the balcony, and large windows allow natural light to enhance the warm exterior. Nearby trees provide a shaded area along the brick pathway.

Home in Winchester

4.93 out of 5 average rating, 159 reviews

Historic District Charm On Cameron Street

Charming home located in the historic district of Winchester. A short walk to the walking mall,restaurants, shopping, farmer's markets,breweries and more. Convenient to Shenandoah University, Winchester Medical Center, many museums including the Museum of the Shenandoah Valley, George Washington Hotel, Skyline Drive, 81 and more. Big deck and a half court basketball in the back yard. We have added a work/office area with a desk and chair ideal for working or schooling from home.

Guest favorite

A welcoming living area features a patterned couch adorned with soft pillows, positioned under warm lighting. A small coffee table rests in front, and a TV stands on a wooden console. Minimalist decor includes floral artwork on the wall, complemented by wooden accents.

Guest suite in Winchester

4.81 out of 5 average rating, 350 reviews

Safe, cozy oasis with private living & bath.

Wonderfully comfortable basement apartment. We are less than a mile from Winchester Medical Center.... ideal for traveling doctors/nurses. Close to other area attractions. You will have your own living room, bathroom and bedroom. Private entrance. Digital lock. You will get instructions prior to check in. You will be in the basement however it has natural light in the bedroom. There may be some noise from upstairs, but it is generally quiet.

Guest favorite

An open-concept kitchen and living area is presented, featuring modern cabinetry and stainless steel appliances. A cozy armchair with a blue cushion sits beside a small table, while barstools line the kitchen counter. A patterned table adds a splash of color to the space.

Townhouse in Winchester

4.93 out of 5 average rating, 258 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.

Top guest favorite

A charming stone cottage with a wooden front porch features a sloped roof and a brick chimney. Surrounded by trees, the cottage is set on a grassy area, providing a sense of seclusion. Large windows and a welcoming entrance enhance the exterior appeal.

Cottage in Winchester

4.97 out of 5 average rating, 516 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.