Places to stay in Winchester

4.99 out of 5 average rating, 407 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...

Superhost

A spacious living area features a comfortable beige sofa adorned with textured throw pillows. Natural light enters through large frosted garage doors, revealing a view of outdoor trees. A wooden dining table is visible in the background, enhancing the open and inviting space.

4.9 out of 5 average rating, 354 reviews

Downtown 1920's Gas Station with Hot Tub

Luxury 1920’s Refurbished Gas Station and hot tub repurposed into a beautiful apartment. Private parking/EV charging station, 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, coffee nook, and 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!

4.97 out of 5 average rating, 143 reviews

A cozy cabin interior features wooden walls and ceiling accents. A sliding barn door leads to a bathroom space, and a comfortable couch is positioned nearby. Artwork and decorative elements add character, while a ceiling fan is visible, enhancing the inviting ambiance of the room.

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 vibrant street scene is depicted, featuring outdoor dining with umbrellas providing shade. Lush greenery and colorful flowers line the railing, enhancing the inviting atmosphere. A mix of pedestrians strolls along the brick walkway, surrounded by charming buildings and a clear blue sky.

4.97 out of 5 average rating, 196 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 !

A historic archway welcomes visitors to Old Town Winchester, illuminated by streetlights through gently falling snow. Snow covers the ground, leading down a pathway lined with trees. Buildings with traditional architecture and a mix of shops can be seen on either side.

5 out of 5 average rating, 209 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.

The entrance features a dark brown door set within a brick wall. A decorative wreath made of orange flowers and branches is prominently displayed on the door. A small sign indicating the apartment number is positioned above the door handle.

4.97 out of 5 average rating, 283 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.

Superhost

A warm-toned living area features a staircase leading to an upper level. The kitchen area is visible in the background, equipped with cabinets and appliances. A wooden dining table sits in the foreground, complemented by a cozy seating area with a patterned couch.

Loft in Winchester

4.72 out of 5 average rating, 658 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!

A set of wooden shelves mounted on a light blue wall displays a cozy gray blanket, a decorative basket, and a small potted plant. A framed sign with a welcoming message is positioned above the items, adding a personal touch to the space.

4.97 out of 5 average rating, 254 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.

A quiet downtown street is depicted under a twilight sky, with a mix of historic buildings on either side. Soft streetlights illuminate the cobblestone road, which is lined with a few parked cars, creating a welcoming atmosphere for evening strolls.

4.95 out of 5 average rating, 190 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

4.81 out of 5 average rating, 339 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, 245 reviews

A welcoming entrance to Old Town Winchester is showcased, featuring a prominent archway with the text 'Old Town Winchester.' Lively shops and cafes line the pedestrian mall, which is adorned with trees and outdoor seating beneath umbrellas.

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.

A hot tub is situated on a paved area surrounded by stone, featuring a textured design. The tub is covered with a black lid, offering an appealing contrast to the greenery of the yard. A grill is partially visible underneath a protective cover nearby.

4.97 out of 5 average rating, 233 reviews

Full basement with private entrance. Hot tub

Cozy movie themed basement is exactly what you are looking for. Classic AirBnB-we are opening our house to you! Space is completely private. Bedroom with queen bed. High speed internet. Private bath w/shower. Small refrigerator, microwave, 2 flat screen TVs table and chairs and multiple couches in a large family room w/Sofa bed. 1000 square feet of space! Home 2 miles outside of the city of Winchester in Frederick County.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Winchester places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Winchester

A well-maintained staircase leads to the upper floors, flanked by neutral walls and wooden trim. A stylish chandelier hangs from the ceiling, illuminating the hallway. A small table with a lamp and a potted plant are positioned along one wall, enhancing the welcoming atmosphere.

4.95 out of 5 average rating, 77 reviews

Easy like a Sunday Morning 1 BR apt great location

Guest suite in Winchester

A welcoming entrance is showcased with brick steps leading up to a blue door, adorned with a floral wreath. Two chairs with bright green cushions are positioned on either side of the entrance, complemented by neatly arranged yellow flowers and a small shrub.

4.93 out of 5 average rating, 58 reviews

Retro Vibe Studio

A wooden bridge spans over a gentle stream, surrounded by lush greenery. The bridge's railing is made of slender metal bars, providing a safe passage through the serene landscape. Sunlight filters through the trees, casting subtle shadows on the water below.

5 out of 5 average rating, 33 reviews

Whole 3-bedroom house walkable to downtown.

A pair of white appliances are positioned side by side, featuring a washing machine on the right and a dryer on the left. Both machines have clear control panels displaying various settings and dials, set against a neutral wall.

4.95 out of 5 average rating, 60 reviews

Misty Meadow has quite setting in the country.

Superhost

A compact kitchenette is visible, featuring a stainless steel refrigerator, microwave, and coffee maker. Silverware and glassware are neatly organized on shelves alongside snacks and a pie dish. The space is designed for convenience, with essential items accessible for guests.

4.65 out of 5 average rating, 37 reviews

The Flat of Old Town Winchester

5 out of 5 average rating, 27 reviews

A covered deck extends from the cabin, featuring comfortable seating arrangements and a grill for outdoor cooking. The wooden flooring adds warmth, while views of the surrounding nature create a peaceful setting for relaxation.

Cabin in Culpeper

Campo Cibola - Brisa

4.99 out of 5 average rating, 79 reviews

Home in Berryville

Deer Chase