Vacation rentals in Winchester

4.99 out of 5 average rating, 412 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

Uber SXY 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...

4.97 out of 5 average rating, 146 reviews

A cozy living space features a wooden ceiling and light-colored walls. A small electric fireplace is placed beneath a wall-mounted television. A coffee table sits centrally, surrounded by two comfortable chairs and a couch, with a front door visible to the side.

Cabin in High View

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

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.

4.97 out of 5 average rating, 198 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 !

4.99 out of 5 average rating, 200 reviews

A spacious bell tent is positioned on a wooden deck, surrounded by natural stone and lush greenery. Soft lighting is visible inside, enhancing the inviting atmosphere. Sturdy steps lead up to the tent entrance, framed by earthy tones and the sounds of nature.

Campsite in Front Royal

Blue Mountain Hideaway • Enchanting Glamping Stay

Unplug and unwind at Blue Mountain Hideaway, a boutique glamping tent nestled in the woods near Shenandoah National Park and the Shenandoah River. Enjoy a real bed, a fully equipped outdoor kitchen, and complimentary firewood—no WiFi, no distractions, just the sounds of nature. Cozy up by the fire, savor slow mornings, and reconnect with what matters most. Just bring your cooler and clothes—we’ll handle the rest. Perfect for couples, solo travelers, and anyone craving a quiet place to reset.

5 out of 5 average rating, 212 reviews

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

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.

4.98 out of 5 average rating, 158 reviews

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

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.

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

4.73 out of 5 average rating, 664 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!

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, 256 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.

The inviting living room features a cozy dark blue sofa adorned with various colorful pillows. A red coffee table sits in front, complemented by a soft area rug and warm natural light flooding through the large windows. A beige armchair and decorative accents add to the ambience.

4.95 out of 5 average rating, 191 reviews

Indigo Blue modern open vibe on tree lined street

Come stay in this lovely spacious downtown home located on a beautiful tree lined street. Enjoy its open mid century modern style and relaxing outdoor areas! This 3BR 2BA home w/ sunroom w/ gas fireplace & rear fully fenced courtyard is the perfect place get away to & explore downtown Winchester. Walking distance to everything. Park & walk & enjoy nearby John Handley HS /walking mall /shopping/live music /art galleries/ walk to the iconic Handley Library, You will LOVE it!

Guest suite in Winchester

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.

4.81 out of 5 average rating, 344 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.

4.93 out of 5 average rating, 249 reviews

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

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.

4.97 out of 5 average rating, 503 reviews

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

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Winchester vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Winchester

4.99 out of 5 average rating, 80 reviews

A log cabin is nestled among the trees, featuring a fenced inground pool in the foreground. The pool area is surrounded by a textured patio, complemented by several wooden chairs positioned nearby. The cabin is situated on a gravel driveway, highlighting its private setting.

Cabin in Fort Valley

Hidden in the Valley | Pool | Pets | Fire Pit

Superhost

A bright living area features natural wood ceiling and walls, adorned with shelves holding books and decor. A comfortable sofa, complemented by a round mirror and a textured rug, invites relaxation. A dining bar with stools offers additional seating, enhancing the open atmosphere.

Cabin in Wardensville

5 out of 5 average rating, 3 reviews

The Philosopher’s Retreat

4.99 out of 5 average rating, 81 reviews

A cozy bedroom features a spacious bed with crisp white linens and a soft grey blanket. A decorative red and white pillow adds a touch of warmth. Soft lighting from bedside lamps creates a calm ambiance, while a small fan is mounted on the ceiling.

Farm stay in Strasburg

Homestead with Shenandoah Valley Views

Guesthouse in Stephens City

A welcoming entryway features a covered porch with two rocking chairs positioned on a concrete path. The front door is framed by two large windows, showcasing a panoramic view of the surrounding hills and fields in the distance.

4.78 out of 5 average rating, 18 reviews

Ventura Cottage: 360-views/HotTub/4 acres/Gym

4.95 out of 5 average rating, 77 reviews

A light-filled living area features a cream-colored sofa with yellow accent pillows and a patterned ottoman. A dining table with chairs is visible in the background, along with a large window allowing natural light to illuminate the space.

Apartment in Winchester

Easy like a Sunday Morning 1 BR apt great location

Tiny home in Capon Bridge

A cozy sleeping area features a plush queen-size mattress with luxury linens. Soft ambient lighting highlights the bed, while large glass windows offer views of the river and outdoor Adirondack chairs. Natural wood accents add warmth to the modern cabin design.

5 out of 5 average rating, 32 reviews

Pugh’s Paradise - Riverfront

Apartment in Stephens City

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.

5 out of 5 average rating, 16 reviews

Spacious Charming Basement Apt

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.