Vacation Rentals By Owner In Winchester, VA

Come to downtown Winchester get the true feel of the city. Walk to beautiful Handley Library, take a stroll to the walking mall to the many shops & restaurants. Scarborough Fair is the place to enjoy the time w/family and friends. Three large bedrooms, two levels, three porches, and a completely fenced rear yard. Scarborough Fair is eclectic & comfortable you will love your stay in this wonderful spot downtown. Looking for more space I have several spots in downtown Winchester. Find me: Michele Bouve Hoffman on social media. Happy Travels!brThe spacebrThere is a living room with sofa bed and comfortable seating for 6-8 that opens into a dining area with mid century table to gather around, desk work space and fold out futon for additional guests. The modern kitchen is fully equipped with all the amenities you will need for your stay including large pantry with washer and dryer. Up the staircase to second floor is the full bath with tub and three spacious bedrooms: back bedroom has bunk bed ( twin over full) , and 2nd flat screen tv ( ROKU) middle bedroom has queen bed and is a walk thru (each bedroom has own door for privacy). Front bedroom has a queen bed and sitting area.brThe upper, rear and front porches are great for relaxing. Enjoy the porch rocker and listen to the sounds of the church bells ring, walk across the street and grab a book from the library or order a delicious coffee or chai tea from the Expresso Bar on the walking mall. You will love this spot ! See listing photos for wifi info. PLEASE NOTE: brAll major holidays ( Local: Apple Blossom brNational: Christmas/ Thanksgiving/ New years/4th of July /Memorial and Labor Day ) will include an additional $100 fee. This fee will be requested prior to guests arrival.brbrPlease NOTE: brStays over 3 weeks will incur an additional double cleaning fee.brbrQuiet Hours: 10pm to 7am.

Scarborough Fair walk to downtown two story apt

Winchester, Virginia, United States

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Exceptional(8)

$165.42

This little place is just plain charming.brLots of light and personality.brWonderful alternative to the typical hotel experience.brFabulous for short term rental needs.brCome enjoy DowntownbrFlat screen TV/ Record Player FREE PARKING/WIFIbrNear Piccadillys Pub, the Walking Mall, our beautiful and historic library, Shenandoah Univ. -5 minute Winchester Med Center -5 min DC. -1.5 hr Skyline Drive -30 minbrFree Parking too !brbrReach out on social media if you need more. Michele Bouve HoffmanbrThe spacebrThis vintage apartment above downtown shop is just plain charming. It is decorated with lots of light - and personality!brEnjoy your morning coffee on the porch swing and wait for the train to come by. The main bedroom has a queen sized bed and large closet. There is a turntable and some vinyl there for your enjoyment.brMany guests have been delighted with their stays and have said that the apt. is more spacious than it looks in pics .br

Pretty Little Apt by the Train II

Winchester, Virginia, United States

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Exceptional(1)

$199.41

Welcome to the Stock Exchange locatedbrat 406 N. Loudoun Street Apt. #11.brCome away to this great 3rd floor studiobrwith kitchen and bath & comfortable full sized FUTON.br(https://minimalistvibe.com/are-japanese-futons-good-for-your-back/)brThis small one room studio is open and airy with lots of windows! You are justbrone and a half blocks up from the marvelous Winchester walking mall. There is free on site parking so you can just park your car and spend the rest of your time on foot! Enjoy !brThe spacebrNicely decorated studio efficiency with large flat screen TV on the third floor overlooking Winchester. The downtown walking mall offers a unique shopping experience and a Saturday Farmers Market within walking distance.

The Stock Exchange downtown 3rd floor studio apt

Winchester, Virginia, United States

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Exceptional(8)

$350.1

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.brCome spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !brThe spacebrOver 1600 square feet of lavishly renovated space where the local builder has taken great care to retain the innate charm of Old Town Winchester. Open and airy, uncluttered and refined-- those who want to be pampered a bit and like a clean and rich feel will find Cameron Charmer does not disappoint !

Cameron Charmer pristine downtown apt with double master suites

Winchester, Virginia, United States

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Exceptional(2)

$63.18

Individual loft apartments with front patios. Walk in to a living area and connected kitchenette with refrigerator. We supply dishware, silverware, toaster, coffee maker and pots and pans to use on the 2 burner stove top. Large shower and loft bedroom with a second TV. A home away from home.

Lofts for weekly rentals! 2 miles from historic downtown.

Winchester, Virginia, United States

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Exceptional(9)

$260.52

Your home away from home in Winchester with 3 bedrooms. This superb single home features 1 king bed, 1 queen bed, and 1 full bed and a futon. perfect for a pleasant stay. Enjoy the convenience of WiFi, a washing machine, heating, and AC. With 2 full bathrooms and 1 half bathrooms an additional office space with a futon, this wonderful property has everything you need for a comfortable stay. Fall in love with Winchester and enjoy the magic it has to offer.

New Charming 3-bedroom 2 full bath and 1 half bedrooms Single family house

Winchester, Virginia, United States

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Exceptional(33)

$153.55

Renovated colonial style home. Enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms with 4 beds and 2.5 bathrooms. Perfect for a larger group 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 -Skyline Drive, Luray Caverns, and Harper's Ferry! brbrThis house has been a long term rental for 12 years but it was our first home and the start of our family so it will always be special. We enjoy this experience so much with our other property that we decided to renovate it and do another vacation rental! brbrThe house is fully equipped with everything you need to cook with and all the linens you could need. Full size appliances--fridge, stove & dishwasher. Washer and dryer on the main level. Upstairs is a King bed in the master and three Full beds. A shower in the Master bedroom and shower/tub on the 2nd level as well. All bedrooms are upstairs. A pack and play portable crib and dining booster seat is available for babies. Living room has a 50 inch tv with large sectional sofa. Kuerig machine for coffee drinkers.brbrPlease only park in the driveway. No street or yard parking is permitted. Please remove shoes before walking on upstairs carpet. Smoking outside only. br

Colonial Getaway near Old Town Historic Winchester

Winchester, Virginia, United States

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Exceptional(20)

$105.21

Welcome!brNestled 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 by car, sits this charming and quaint carriage/guesthouse on 2+ secluded acres known as 'The Secret Gardens Guest House'. brbrThe Carriage House dates from the 1920’s and features a bedroom with an antique double four-poster bed, full bathroom with old-fashioned pedestal tub with safety bar and shower, beautifully updated kitchen, a private cafe style screened-in porch overlooking a gorgeous view of Zen Gardens and much more!brbrThe charm and grace of this intimate cottage is lovely. The vibrant décor blends past and present with unique elegance. You can easily imagine a tasseled buggy pulling up as you enjoy the pleasure of modern conveniences. brbrThe year round natural beauty framing our adorable Carriage House is unparalleled in Winchester. More than two acres of exquisite Zen Gardens are just a few steps away. Guests love spending time on our screened in porch, taking in a view that brings the blooms of the season to your doorstep as you sip your morning Organic coffee or tea in fresh robes that we provide for every guest. All of the environments inside and out are over seen with no chemicals used. This being the case we ask that you not use chemical cleaners or scented products that may impact the space. brbr In truth, the photographs of the Gardens on this site, simply don’t do it justice. It is a one-of-a-kind experience.brbrOur Organic herbal and veggie garden – where guests are welcome to choose fresh herbs/veggies for their dining pleasure – offers another special treat. brbrWe have an outdoor fire pit area, ideal for star gazing that just can’t be appreciated in the downtown lights. Or you could take the time to sit by our fire pit with a warm mug of Organic coffee or Organic tea while listening to the soft sounds of the season, lifetime memories with that special someone are created.brbrWe also welcome business travelers wanting more than an efficiency apartment as well as lone adventurers. Every time of the year is special in this sanctuary from the busy world.brbrAs the Carriage House is a delicately crafted setting, guests must be at least 21 years old.brbrThe guest house offers the simplicy of living. While Wifi may be available, there is no TV on site. You are more than welcome to bring your own devices and stream what you like if you need more stimulation. brThe kitchen is fully equiped other than a microwave. Again, simplicity of living. brbrShort stays or long, you will be embraced by the quiet space and open gardens.

Guest House

Secret Gardens Carriage House

Winchester, Virginia, United States

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Exceptional(4)

$213.14

This bright 3BR house (2 queens, 1 full, 1 twin) is ideal for families, travel nurses, business travelers or vacationers in the area. Enjoy a full kitchen, fast WiFi, Smart TV, washer/dryer, very large yard and driveway parking for 3-4 cars. Located just 15 mins from Winchester Medical Center and 8 mins to Old Town or Shenandoah University, 7 mins to Costco and 10 min to Walmart or Target. Close to I-81, wineries, and hiking trails. Clean and quiet.

Charming 3-bedroom house with porch and yard in Winchester

Winchester, Virginia, United States

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$204.18

Apartment in Winchester, pet friendly! We live on 5 acres nestled in our own little piece of heaven, located in Shenandoah Valley. We raise chickens and bees. This is a beautiful country getaway perfect for relaxing with a nice drive to old town Winchester.brbrThis peaceful apartment is very clean, clutter free and almost everything is fairly new. It is super cozy and comfy with a private entrance and a secure electronic lock. You can enjoy the deer passing through the property from time to time. We also take the time to follow CDC guidelines to ensure your safety and ours.brbrPlease feel free to walk any area of our property outside of the fenced in area. Keep a comfortable distance from the beehives especially if you have allergies.brWe do sell our raw honey and fresh eggs let us know if you're interested. Payable in cash.

Cozy Apartment located on our 5-acre property

Winchester, Virginia, United States

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Exceptional(14)

$235.27

Lovly cabin on a farm stay, oversized livingroom kingbed full kichin large front porch to watch the vally views.

Cabin on a farm stay with roaming peecocks

Winchester, Virginia, United States

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$199.14

Spacious home, desirable neighborhood, two minutes from the medical Center in Winchester. Three bedroom 2 1/2 bath, house with patio area, full kitchen and everything you need, Beautiful landscaping. Just minutes from the medical complex and downtown. Walking mall.

Spacious home, near medical center, Winchester

Winchester, Virginia, United States

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Bath

Sleeps

Exceptional(7)

$165.6

Nestled in the picturesque city of Winchester, the Queen of Winchester offers a tranquil escape in a prime location that perfectly blends convenience and comfort. This beautifully renovated three-bedroom apartment is situated on the upper level with a terrace deck, promising privacy and views of the surrounding area. Whether you're visiting for a relaxing retreat or a business trip, this property is designed to ensure a memorable and luxurious stay.brUpon entering the Queen of Winchester, you are greeted by a modern and stylish interior. The apartment features three spacious bedrooms, each thoughtfully designed with contemporary decor and cozy bedding to provide the perfect setting for a restful night's sleep. Large windows allow natural light to flood the rooms, enhancing the airy and welcoming atmosphere.brThe living area is the heart of the apartment, where guests can unwind and relax. It's equipped with comfortable seating, a state-of-the-art entertainment system, and tasteful art that adds a touch of elegance. The space opens up to an upper-level terrace deck, an idyllic spot for morning coffees or evening drinks while taking in the serene views of Winchester's landscape.brThe kitchen in the Queen of Winchester is a chef's dream. It is fully equipped with modern appliances, including a refrigerator, stove, microwave, and dishwasher. Ample counter space and a variety of cooking utensils make it easy to prepare meals, from quick breakfasts to elaborate dinners. Adjacent to the kitchen is a charming dining area that seats six, ideal for enjoying home-cooked meals or hosting dinner parties.brOne of the apartment's highlights is its location. Conveniently located off Interstate 81 and close to downtown Old Town Winchester, guests have easy access to a range of attractions and amenities. Explore the historic streets of Old Town, where you can visit unique shops, local eateries, and cultural landmarks. Winchester Hospital is also nearby, making the apartment a perfect choice for medical professionals or families visiting patients.brSafety is a priority at the Queen of Winchester. The apartment is a separate unit above the Juliana MedSpa, ensuring privacy and security. The area is well-lit, and ample parking is available, making it easy for guests to come and go as they please. Additionally, being next to FoodMaxx, an international grocery store, means that everything from exotic spices to daily necessities is just a stone's throw away.brFor those who appreciate the convenience of location without compromising on tranquility, the Queen of Winchester is an ideal choice. Its proximity to major highways and downtown, coupled with the privacy of an upper-level apartment, offers the best of both worlds. Whether it's exploring the historical charm of Winchester, conducting business, or seeking a peaceful retreat, this property caters to all needs.brMoreover, staying above a MedSpa has its perks. Guests can book appointments for relaxing treatments just downstairs, adding an element of luxury and convenience to the stay. From soothing facials to therapeutic massages, the spa offers a range of services to rejuvenate both body and mind.brIn summary, the Queen of Winchester is more than just a place to stay; it's a destination that offers a unique and enriching experience. From its chic, comfortable interiors and stunning terrace views to its unbeatable location and safety features, every aspect of the apartment is designed to provide an exceptional stay. Discover the charm of Winchester and indulge in the luxury and convenience of this exquisite rental property. Whether for a short visit or an extended stay, the Queen of Winchester welcomes you to enjoy all that it and the city have to offer.

The Queen of Winchester Three Bedroom with Upper Level Deck

Winchester, Virginia, United States

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$156.63

Separate back entrance. Spacious fully finished walk out basement with fully furnished. It has two bed room . 1st bedroom has 1 queen bed and 2nd bedroom has two full bed . Air mattress is also available for extra person . Full kitchen with dining area. Big Living room has big screen and Projector.

Very charming & spacious 2 bedrm

Winchester, Virginia, United States

Bed

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Exceptional(5)

$163.2

Mountain top getaway! A cozy two bedroom house on the top of a majestic mountain with picturesque views that you will fall in love with. It is less than thirty minutes from downtown Winchester and nature trails right outside the door. Historic civil war battlefields, wineries, and Luray Caverns are also in the surrounding area

Mountain top getaway with the best view ever!

Winchester, Virginia, United States

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$261.25

Make yourself at home in this 3-bedroom Winchester retreat. This fabulous house features 2 queen beds and 1 twin bed, perfect for a cozy stay. With amenities like WiFi, a washing machine, and heating, guests will feel right at home. The 4 bathrooms come equipped with a hairdryer and bathtub for added convenience. We hope you enjoy what our place and Winchester has to offer.

Charming 3-bedroom house in wonderful Winchester with WiFi, AC

Winchester, Virginia, United States

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$188.58

Welcome to Kona’s Cabin — Your Cozy Shenandoah EscapebrbrUnplug, unwind, and settle into Kona’s Cabin, a private and pet-friendly retreat just minutes from Shenandoah National Park, historic downtown Winchester, hiking trails, wineries, and breweries. The cabin features an open living area, cozy fireplace, and a well-equipped kitchen for all your cooking needs.brbr Kona’s Cabin blends rustic charm with modern comfort. Inside, you’ll find a warm, thoughtfully designed space with a fireplace, comfortable seating, and everything you need for a relaxing stay. Step outside to enjoy the firepit, fresh mountain air, and peaceful surroundings.brbr ‍ ‍ The cabin comfortably accommodates up to six guests with three bedrooms, each furnished with soft bedding and linens. The bathroom features an updated shower with gold fixtures and fluffy towels. Our spacious living area boasts a crackling fireplace, comfortable seating, and large windows that bring in plenty of natural light. The fully-equipped kitchen makes preparing meals a breeze, and the peaceful bedroom ensures a restful night’s sleep.brbr Working remotely The cabin has ultra high-speed WiFi that can handle multiple video calls and a smart TV with streaming services.brbr Outside, guests can enjoy the beauty of the forest from the comfort of our spacious patio, complete with comfortable seating, charcoal grill and an outdoor firepit. For those seeking adventure, there are numerous hiking and biking trails nearby, as well as opportunities for kayaking, fishing, skiing, horse back riding, tubing, and other outdoor activities.brbr ️ Beyond the cabin itself, we’re a short drive away from many popular tourist destinations in Virginia and West Virginia:br- Historic Downtown Winchester (20 minutes) — tons of restaurants, bars, cideries, wineries, breweries, and more!br- Berkeley Springs (45 minutes) — great shops and restaurantsbr- Shenandoah National Park (45 minutes) — miles of hiking and views galorebr- Harpers Ferry (55 minutes) — scenic views, tubing, kayaking, and morebrbr⛰️ General activities around the cabin:br- Hiking (Great North Mountain, Appalachians, and Shenandoah National Park)br- Breweries, cideries, and wineries (over 30 within a half hour drive)br- Swimming, fishing, canoeing, tubing, and boatingbr- Paintball, ATVing, and go kart tracksbr- Horseback riding lessonsbr- Drive-in movie theatre, axe throwing, escape rooms, and more!

Kona's Cozy Cabin — King Bed, Fireplace, Pet Friendly, Near Hiking and Wineries

Winchester, Virginia, United States

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Most popular vacation rentals in Winchester

$331.97

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Winchester, Virginia, United States

Bed

Bath

Sleeps

$105.21

Guest house

Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

Winchester, Virginia, United States

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Bath

Sleeps

$137.66

Private vacation home

City Charmer near Historic OldTown Winchester.

Winchester, Virginia, United States

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Bath

Sleeps

$138.75

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Winchester, Virginia, United States

Bed

Bath

Sleeps

$153.55

Private vacation home

Colonial Getaway near Old Town Historic Winchester

Winchester, Virginia, United States

Bed

Bath

Sleeps

$178.68

Morocco Loft 2BR overlooking city walking mall

Winchester, Virginia, United States

Bed

Bath

Sleeps

$309.90

Country House

Modern 3BR Farmhouse in the Country

Winchester, Virginia, United States

Bed

Bath

Sleeps

$156.23

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Winchester, Virginia, United States

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Bath

Sleeps

$244.86

Cabin

Dog Friendly Mountain Retreat with Stunning Views

Winchester, Virginia, United States

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Bath

Sleeps

$165.42