Vacation rentals in Winchester

4.99 out of 5 average rating, 403 reviews

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...

A grand building is displayed featuring classical architecture with prominent columns and a domed structure on top. Steps lead up from the well-maintained lawn, bordered by evenly spaced trees, emphasizing the building's inviting presence in the landscape.

4.82 out of 5 average rating, 128 reviews

The Comfortable In-Towner

A cute one bedroom apartment located on lower level of a historic 1840s home. This half basement has windows to let in natural light, a full-size kitchen with dishwasher, fridge, big closets, Queen size Tuft & Needle premium mattress and a private screened patio open to our courtyard with friendly neighbors and management on site. Window ac units, fans & radiators Quiet neighborhood in Old Town Winchester, Va, two short blocks from pedestrian mall with restaurants, shops cafes & entertainment.

A spacious area showcases a combination of modern and rustic design elements. Large glass garage doors provide an open view of the inviting living and dining space, which features a dining table with chairs and a cozy seating arrangement illuminated by soft lamps.

4.9 out of 5 average rating, 350 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, 141 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, 206 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, 280 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.

4.73 out of 5 average rating, 656 reviews

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

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, 253 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, 188 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!

4.93 out of 5 average rating, 241 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.

4.97 out of 5 average rating, 496 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.

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Popular amenities for Winchester vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Winchester

A close-up view of three dark leather dining chairs positioned beside a white table. The rich wood flooring creates a warm contrast, while the staircase is visible in the background, highlighting a contemporary design element.

5 out of 5 average rating, 56 reviews

Downtown Chic Condo w/parking

SaraRating, 5 stars1 month ago

Very, very cute place, especially for a solo traveler or couple. Location-wise, it couldn't be better for walkability for old town Winchester. If you are in the TV room, you will hear a lot of car noise from the street, which is expected with the location, as it is a row house on one of the old town main streets (Which also makes it convenient). I was able to sit and watch tv but it is noticeable in that room in particular. When I went up to bed, it didn't bother me in the least upstairs. There is also a white noise machine provided if needed. I walked to anything I needed and I slept very well. The parking spot was super nice to have. Highly recommend!

5 out of 5 average rating, 52 reviews

Large Historic Stone Home in the Heart of Old Town

PatRating, 5 stars1 day ago

I rented this out for my son, daughter and their families while they were in town visiting me. They loved the space and were impressed with the outdoor area and different sitting areas. It was so convenient to the restaurants and the walking mall.

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.

GiniRating, 5 stars2 months ago

We thoroughly enjoyed our extended stay in this charming cottage! The location is ideal for walking—- either around the neighborhood or downtown. We loved the charm and cozy atmosphere and spent a lot of time on the sun porch too! Can’t recommend it highly enough and look forward to staying here again

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, 57 reviews

Retro Vibe Studio

AndrewRating, 5 stars1 month ago

Fantastic host. Easy to communicate with and the town was easily walkable. Really enjoyed the very short walk to the hill behind Handly high school to see the blue ridge mountains in the background at dusk! Would stay here again!

4.89 out of 5 average rating, 9 reviews

Skyview Farmhouse

Susan & JimRating, 5 stars5 days ago

A beautiful farmhouse in a lovely setting. We really enjoyed our stay. The house has everything you need to cook and be happy. And Denise checked in to make sure we had everything we needed. I would definitely stay there again.

4.99 out of 5 average rating, 77 reviews

Home in Berryville

Deer Chase

MistyRating, 5 stars2 weeks ago

Fast and easy communication. The place was beautiful, clean, well stocked, and easy to access. Had a lovely stay and would def would recommend the place and Jeanne.

4.94 out of 5 average rating, 82 reviews

Cabin in Winchester

Foxtrot Mokki | Springtime Getaway 2 Hours from DC

JoshuaRating, 5 stars1 week ago

This oasis in the woods was worth every dollar. The host was incredibly responsive and extremely accommodating. He was super friendly and we enjoyed every minute of being here. Highest recommendation!