Home Vacation Rentals By Owner In Winchester, VA

Showing 20 Of 38 Vacation Rentals
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$178.68

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Morocco Loft 2BR overlooking city walking mall

Winchester, Virginia, United States

Welcome to Morocco Loft ~ this is a large loft on the third floor of a vintage tudor style building high up overlooking the downtown cityscape with lots of character and charm. You will love the trendy decor and unique layout just steps from the downtown walking mall, discovery museum and the many unique shops and restaurants of Winchester.
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$159.46

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Stunning Mountain Top 1 Bedroom Apartment - Walk-out Basement

Winchester, Virginia, United States

Get ready to relax in this 1-bedroom apartment (walk-out cabin basement) at the top of a mountain with gorgeous views of the Shenandoah Valley! This lovely space features a cozy queen bed in the spacious bedroom and a nice sofa bed in the living room, to include an extra seating area, kitchenette, and dining space. Guests can enjoy outdoor amenities like a fire pit, gas fire table, propane grill, and more.
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$180.24

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Dragonfly Inn Modern 1 BR 1BA downtown apt. Great walking location !

Winchester, Virginia, United States

You will love this new updated downtown apt ! Come stay @ the Dragonfly Inn full of light and whimsy …it’s just one block from the walking mall in downtown Winchester, Virginia. Short/Mid/Long Term stays are welcome. Park for free (2 spaces) and be close to everything downtown. Awesome fully furnished newly updated 1BR 1BA 2nd floor Apt. Washer Dryer in the unit. brALL utilities included /WiFi -600/ SMART TV in Living Rm and Bedroom Streaming ROKU /Nice tiled bathroom w/glass shower/Fully equipped eat in kitchen w/gas stove/spacious fridge! brThis apartment is within walking distance from almost everything downtown Winchester. brTwo designated free parking spots. brCome park your car —check in and relax and enjoy ! brDo not miss:br*the iconic John Handley Library - br*George Washington Hotel’s Half Note Lounge /live entertainment br*Bright Box - music venue on walking mall. br*Museum of the Shenandoah Valley- 15 min walkbr*Discovery Museum - 5 min walk br*Knead Bread / Bakery on Piccadilly St. br*Expresso Bar great coffee on walking mall br*Violinos Restaurant (Italian~ fancy ) br*Macados -huge deli sandwiches br*Romas -fab pizza and pasta br*Vibrasa - beer garden/ food on Kent St.br*El Centro ( Mexican ) Walking mall br*Chopsticks (Thai) on Kent St. br*Hopscotch Coffee on Millwood Ave ( vinyl and great coffee) br*Amherst Diner br*Bonnie Blue incredible food on Amherst st br*Handiworks Gallery -unique gifts brKimberly’s Gifts & Ice Cream on Braddock brbr— you’ll love these spots !brbrAlso if you are interested in moving to the area I have been a licensed Realtor in Virginia and West Virginia for over 20 years and I would be happy to help you find your perfect house ! br***Please be respectful of your neighbors .brQuiet hours are 10 pm to 7 ambrImportant Please NOTE: brWe do not raise our nightly prices over MAJOR HOLIDAYS and over our local APPLE BLOSSOM instead we charge a flat $100 holiday fee — please understand this is in addition to your initial payment and the request for it will be sent out the week before your arrival thru your VRBO account. brHOUSE RULES : brNo Smoking or Vaping brNo pets w/o prior approval brNo parties of any kind brNo drama please … brWe love being able to host our guests !!brPlease leave the apt as you found it when you depart.
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$121.42

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Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly

Winchester, Virginia, United States

Welcome to your cozy 1-bedroom apartment at Brookfield Corporate Apartments in Winchester, VA! This fully furnished unit offers a comfortable living space with all utilities, internet, and cable included. Located in a quiet, convenient area, you'll have easy access to local shops, restaurants, and historic downtown Winchester. Perfect for short or long stays. Enjoy a hassle-free experience with all the comforts of home.
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$137.66

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City Charmer near Historic OldTown Winchester.

Winchester, Virginia, United States

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and a 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.brbrThis home was my grandma's home so even with a fresh new look, it will always be special to me. I visited my grandma in this home for over thirty years and always admired the character of it. While renovating, it was so important to me to keep some of that original charm--from the custom-made cabinets to the original hardwood floors; It's all there just spruced up a bit! brbrOur home has two bedrooms--a queen size bed, full bed, and a pull out sofa with queen size mattress. We also have a pack & play for infants. The kitchen has all the cooking essentials, microwave and a Keurig machine for coffee. There is also a charcoal grill out back. Laundry is available in the basement. The steps are steep so please be careful.br
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$174.77

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Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Winchester, Virginia, United States

Dreamweaver is a light filled colorful 1BR 1BA apt with a futon couch on the 2nd floor. Just two blocks from downtown pedestrian walking mall ! Free on site parking & coin laundry in basement. brEverything is provided for you come stay unwind & relax ! Walk to the iconic Handley Library or drive up to Bears Den for day hike! Visit Skyline Drive, or the Family Drive In, Discovery Museum w/ Rooftop fun, Museum of the Shenandoah Valley fabulous gardens & tons of history to explore! You”ll love it! Could possibly sleep 3 if needed because there is a futon couch in the living area. ( please let us know if you will need extra linens )
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Exceptional(2)

$133.69

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Rosamond nice downtown studio apt

Winchester, Virginia, United States

Come enjoy to this fabulous 3rd floor one room studio apt with kitchen and bath( with tub) & comfortable queen sized mattress. This apt is open and airy with lots of windows and desk and nice closet space. You are just a couple of blocks from downtown walking mall. Free parking and coin operated laundry on site. You will LOVE it !
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$156.23

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

Winchester, Virginia, United States

Cleveland Park is a bright 2 bedroom ground floor apartment just two blocks away from the heart of the city the much loved walking mall. It is an older building but has a charm that will delight you —Its crazy convenient to be within walking distance to downtowns local shops, live music, art studios, delicious restaurants and much more.
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$91.8

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Charming Loft In Winchester Va, Furnished and all Inclusive

Winchester, Virginia, United States

Your cozy studio loft in Winchester with 1 queen bed. This charming retreat offers AC, WiFi, Direct Tv, ALL INCLUSIVE & FULLY FURNISHED, convenience of a washing machine. The serene bathroom features a refreshing shower. Book now and enjoy everything this studio has to offer.
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$83.5

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Sean's Bar Cozy Irish Retreat

Winchester, Virginia, United States

pWelcome to Sean’s Bar, a unique lower lever apartment just off I-81 and minutes from downtown Winchester. Designed with charm and convenience, this cozy space offers a comfortable stay./pbrbrpInspired by Sean’s Bar, the oldest pub in Ireland, this apartment captures the warmth and character of an authentic Irish pub. Whether you're visiting for business, a weekend getaway, or just passing through, you'll love the inviting atmosphere.brbrPlease be careful when enetering as it goes down steps to the basement./p
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$227.73

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Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Winchester, Virginia, United States

brCome stay @ the Dragonfly Inn II - trendy 2 BR 1BA apt on 2nd floor just one block up from the walking mall in downtown Winchester, Virginia. Short/Mid/Long Term stays welcome. Guests will have their own free designated parking space.brALL utilities included /WiFi -600/ Washer & Dryer/Living Rm w/Smart TV /Nice tiled bathroom w/glass oversized shower/Fully equipped kitchen w/gas stove/spacious fridge/stackable washer and dryer ! This modern fully renovated apartment offers a comfortable stay for up to three guests. It features two bedrooms, including one queen bed and one twin bed, perfect for small families. You will love it !
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Exceptional(16)

$217.6

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Cabin

The Overlook

Winchester, Virginia, United States

Cozy up and get away to our tranquil A framed Cabin we affectionately call The Overlook; where you'll enjoy a 360-degree view of the Shenandoah Mountains. Soak in our breathtaking views no matter the season and escape to the peace and quiet our cabin provides.brRelax by the fire at night, hike the beautiful trails nearby, enjoy our famous wineries/breweries, and rest easy in our fully stocked home equipped with everything you could need to get the vacation you deserve!brThe spacebrOur cabin is fully stocked home with everything you'll need for a comfortable stay. Enjoy our fast wifi speed and spacious living room and porch to enjoy the breathtaking scenery around you. Wake up in the morning to a stunning sunrise view of the mountains and feel free to bring lots of friends and family with you as our home has not only three bedrooms upstairs, but a fully finished basement with sleeping arrangements for up to 5 guests!brDon't worry about bringing your supplies from home because we provide it all! Our kitchen is equipped with all cooking supplies, dinnerware, spices, a coffee maker, and more! Enjoy a hot bath or shower fully stocked with soaps and bathroom necessities. Cozy up at night and sit by the fire pit with a glass of wine or lounge inside with reading materials or board games we provide!brGuest accessbrThe Overlook is nestled on the mountain overlooking the Shenandoah Valley with 100+ mile views. Guests have access to the whole home with no shared spaces. This is the only house on that section of the road. The top of the driveway can be a little tricky, but there is plenty of parking for guests. In winter conditions you may need AWD or 4WD. When you book you will receive a personal door code that you can enter on your arrival.brOther things to notebrOur stay allows you to be removed from the hustle and bustle, but be close to enjoying the local wineries, and breweries. You are 20min from historic downtown Winchester VA. Please make sure you keep your trash picked up outside and the trash can locked as we have been known to be visited by bears on several occasions. Please also do not use the fire pits if it is windy as you could start a forest fire.
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$192.61

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Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

Winchester, Virginia, United States

Stunning brand new 1 BR apt within walking distance to everything downtown. Meticulously maintained and beautifully decorated. Full of light and plenty of space to live and work. The apt is overtop of the garage in the rear of another established Airbnb. Designated Free driveway parking spot just steps up to your own private oasis overlooking the treetops. Whether you plan to stay for a night, a week or longer this private relaxing spot will not disappoint! You will LOVE it!
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Exceptional(4)

$138.75

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Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Winchester, Virginia, United States

Stunning brand new 1 BR apt within walking distance to everything downtown. Meticulously maintained and beautifully decorated. Full of light and plenty of space to live and work. The apt is overtop of the garage in the rear of another VRBO rental. There is a nice private driveway parking spot and just one flight of steps up to a brand new IBR I BA oasis overlooking the trees. Come and Walk to enjoy Old Town Winchester. Whether you plan to stay for a night, a week or longer this private relaxing spot will not disappoint! You will LOVE it! High chair and pack and play available upon request.
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Exceptional(11)

$105.21

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Guest House

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

Winchester, Virginia, United States

Nestled within the City of Winchester, Va., in the Shenandoah Valley, 30 Minutes from the Blue Ridge Mountains, sits a charming and quaint Tiny Home on 2+ Acres, known as the “Secret Gardens Tiny Home.” It has a loft with a queen size bed and laundry facilities within for your comfort. In addition, there is a private patio that looks out over one of our beautiful zen gardens. The patio is enclosed for your full privacy should you want it. 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 Secret Gardens Tiny House is accessed from a long driveway with private parking for guests right outside the gate leading directly to the patio and front door. brbrThe private residence of the owners of the estate is just across the driveway as they live on site. brbrLoads of outdoor activity nearby! brbrNumerous restaurants, pubs, shops, and Historic sights and sounds of the beautiful Shenandoah Valley are all within easy driving distance. History enthusiasts will love exploring Historic Downtown Winchester or the many nearby Civil War Battlefields.brbrGuests have access to the entirety of the tranquil and peaceful grounds and may readily enjoy our organic vegetable and herbs; winding through paths that showcase Gardens and Multiple Varieties of Stunning Ornamental Flowers and Shrubs.br brYou can experience a restful & peaceful time sitting by our fire pit with a warm mug of organic coffee or tea.brbrbrAutumn is particularly beautiful at the Tiny Home! Nature's paintbrush touches leaves from trees that throughout our landscape!brbrAll designed to make your stay here to be truly just like heaven!
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Exceptional(24)

$309.9

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Country House

Modern 3BR Farmhouse in the Country

Winchester, Virginia, United States

Welcome to 1891 FarmhousebrbrThe Heart of the Home & Downstairs DelightbrbrStep into a beautifully bright kitchen with features every cook will adore. It effortlessly spills out onto a spacious side porch—ample in size for entertaining, al fresco dining, or simply relaxing while watching the local deer play. Downstairs is completed by a dedicated dining room and a large, welcoming living room.brbrWhile the home features a beautiful original fireplace that adds to the historic charm, it is currently decorative only and not available for guest use. However, we invite you to enjoy the outdoor firepit—we even provide the firewood!brbrUpstairs: History and ComfortbrbrAs you ascend the beautifully angled staircase, the original wood floors immediately capture your attention. This home truly resonates with old-world charm, evident in the gorgeous original doors, knobs, a classic pocket door, and the comforting character of gently sloped floors and windows.brbrThe Master Suite offers a tranquil retreat with a queen-sized bed, a dedicated desk for calls, and free weights and a yoga mat for a quick workout. The second bedroom also features a queen bed and a desk. The bright and cheery third bedroom has two twin beds, both with trundles, perfect for sleepovers!brbrNote: There is no bedroom or full bathroom on the main floor.brbrThe convenient laundry stack is located just outside the hall bathroom for quick cleanups.brbrOutdoor Adventure brHours of fun can be found hanging out in the game shed made from 100 year old barn wood that was previously on the property. The shed features ping pong/pool and arcade games. brbrOutside, guests can also enjoy a volleyball net, corn hole and the possibility of spotting bunnies, deer, turkeys, or even a groundhog on the two-acre property. brbrA charcoal grill is available for your use. brbrAmenities and Location:brbrIn true 19th-century fashion, this historic home sits close to the road that connects you to nearby Winchester and local wineries. This provides quick and easy access for exploring the area, while the large side porch and backyard offer a private space to watch for deer and enjoy the country air. brbrIt's a 2-minute drive to Briede Vineyards and Misty Mountain Meadeworks and a 5-minute drive to Geraghty’s Micro Farm where you can bring back locally grown meats, eggs, honey and more. Six Pastures Farm is less than 10 minutes. Historic Winchester with its dining and shopping is about 15 minutes away. Shenandoah University is two exits down I-81. Clearbrook park is minutes away.brbrWe do not accept long-term bookings. brbrAn EV Car Charger is available for guests.brbrWhile we do have Wi-Fi, the connection can be a bit 'rural' and inconsistent. We like to think of it as a great excuse to put the phones away, grab a board game, and enjoy each other's company. If you’re planning a working holiday that requires heavy Zoom calls, streaming or gaming, this might not be the best fit—but if you’re looking to truly unplug, you’re in the right place!
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$158.13

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Condo

Modern Mid-Century Townhome w Deck near festivals

Winchester, Virginia, United States

Summary:brbrModern multi-level townhome in Winchester, VA featuring stylish mid-century furnishings. Enjoy a lower-level hangout space with Smart TV, Netflix & Prime Video, plus a fully equipped kitchen and Xfinity internet. Ideal for local festivals, Old Town exploring, and Shenandoah Valley getaways—comfortable, convenient, and thoughtfully designed for relaxing stays.brbrbrbrHighlights:brbrSpacious deck & multi-level layoutbrbrSmart TVs + streaming & fast WiFibrbrGreat location for festivals & Old TownbrbrbrbrThe Space:brbrWelcome to your stylish Winchester home away from home. Designed with longer stays in mind, this modern, multi-level townhome is thoughtfully furnished with mid-century modern touches and offers the space and functionality needed to truly settle in. Multiple levels provide room to spread out for work, relaxation, and everyday living, while comfortable furnishings, a well-equipped kitchen, and reliable internet make extended stays easy and comfortable. brbrbrbrWhether you’re in Winchester for work, relocation, seasonal living, or to enjoy the Shenandoah Valley at a slower pace, this townhome offers a welcoming, well-appointed base for stays of 30 days or more.brbrbrbrThe SpacebrbrbrbrSpread across multiple levels, the townhome offers plenty of room for groups to spread out while still enjoying shared spaces together. Natural light, clean modern lines, and warm furnishings create a welcoming atmosphere throughout.brbrbrbrStep outside to the spacious deck—perfect for morning coffee or unwinding after a day exploring Old Town Winchester and nearby attractions.brbrbrbrHighlights:brbrModern mid-century stylebrbrMultiple levels for privacy and spacebrbrComfortable beds and well-appointed kitchenbrbrConvenient location for festivals, shopping, and sightseeingbrbrbrbrBedrooms & Sleeping Arrangements:brbrBedroom 1 (Upper Level Primary Suite) with Queen bed, Smart TV and attached private bathroom with walk-in showerbrbrBedroom 2 (Upper Level) with Full bed and shared full bathroom with Bedroom 3brbrBedroom 3 (Upper Level) with Twin bed and shared full bathroom with Bedroom 2brbrbrbrBathrooms:brbrBathroom 1 (Upper Level – Primary): ShowerbrbrBathroom 2 (Upper Level – Shared): Shower/tub combobrbrBathroom 3 (Lower Level): Shower/tub combobrbrbrbrKitchen & Dining:brbrThe fully equipped kitchen has everything you need to cook and dine comfortably:brbrRefrigerator with ice makerbrbrOven & rangebrbrMicrowavebrbrDishwasherbrbrToaster & toaster ovenbrbrDrip coffee makerbrbrbrbrLiving & Hangout Spaces:brbrLower-level hangout space with Smart TVbrbrStreaming access to Netflix & Prime Video (guests log in with their own accounts)brbrPuzzles and books available for unplugged funbrbrCentral HVACbrbrbrbrConnectivity:brbrHigh-speed internet via XfinitybrbrIdeal for remote work or streamingbrbrbrbrLocation Highlights:brbrGreat stay for Winchester’s local festivals and eventsbrbrClose to historic Old Town Winchester, dining, breweries, and wineriesbrbrNearest grocery store: Martin’s on Pleasant Valley Road (approx. 1.5 miles)brbrbrbrPet PolicybrbrWe’re happy to welcome dogs to join you on your getaway! Please note that due to allergies, we’re unable to accommodate cats. A $29 pet fee applies per furry friend, per night to help cover additional cleaning and care. Thanks for understanding—we look forward to hosting you and your pup!brbrbrbrLonger StaysbrbrFor stays of 14 nights or longer, guests will be asked to e-sign a rental agreement prior to arrival. This agreement helps us comply with local requirements while protecting the property, and will be sent in advance for review.brbrbrbrIn the Area: brbrWinchester offers a mix of history, festivals, outdoor adventure, and small-town charm. Explore Old Town Winchester for shopping, dining, museums, and seasonal events like the Apple Blossom Festival, or enjoy nearby hiking, caverns, wineries, breweries, and river activities throughout the Shenandoah Valley. For guests who love a scenic drive, head east to Virginia horse country and Middleburg to experience polo matches, rolling countryside, equestrian culture, and charming villages—perfect for a relaxed and memorable day trip.brbrbrbrMuseum of the Shenandoah Valley (distance from house 10 mins): Enjoy art, history, gardens, and exhibits celebrating the Shenandoah Valley’s culture and heritage.brbrbrbrShenandoah Valley Discovery Museum (distance from house 10 mins): Hands-on exhibits great for kids and families.brbrbrbrShenandoah Valley Civil War Museum (distance from house 10 mins): Small but highly rated museum focused on Civil War history.brbrbrbrStonewall Jackson's Headquarters (distance from house 10 mins): Historic site featuring Civil War era history.brbrbrbrJames Charles Winery & Vineyard (distance from house 10 mins): Local vineyard offering tastings and wines.brbrbrbrBriede Family Vineyards (distance from house 20 mins): Boutique wine tasting and scenic vineyard views.brbrbrbrOld Town Winchester (distance from house 10 mins): Historic downtown with shops, restaurants, galleries, and seasonal festivals.brbrbrbrApple Blossom Mall (distance from house 10 mins): Large indoor mall with stores and eateries nearby.brbrbrbrAbrams Creek Wetlands Preserve (distance from house 5 mins): Natural walking and birdwatching trails right off Jubal Early Drive.brbrbrbrGreen Circle Trail (runs right next to the home): Scenic walking/cycling trail that runs through Winchester and near MSV.brbrbrbrGreat Country Farms (distance from house 40 mins): Seasonal fruit picking, farm fun, and farm market in Bluemont, VA.
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$64.26

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Hotel

Clean, neat, peace and quiet

Winchester, Virginia, United States

When staying at APM Inn and Suites you will have a choice of a comfy couch, and/or a spacious desk. You will have a bathtub/shower. We have in some rooms a coffee maker, microwave and fridge. We offer free Wi-Fi to all guest and for guest convince we have laundry facilities on site. APM Inn and Suites is located right off of Interstate 81 and route 7. If you feel the need to venture out you are close to hiking, fishing, sight seeing, fine dining and a casino.
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$331.97

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

Winchester, Virginia, United States

If you are coming to Winchester and you want to stay in an elegant renovated loft just steps from the iconic John Handley library and the downtown walking mall… then this is the spot. Hardwood floors, floor to ceiling windows all the charm that a building built in the 1900’s exudes. brGuests will enjoy the fully stocked kitchen, comfortable king size bed, as well as a queen bed room with desk /a sleeping porch with two twins /and pull out sofa bed in the loft for extra guests. You will love it !
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$244.86

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Cabin

Dog Friendly Mountain Retreat with Stunning Views

Winchester, Virginia, United States

Welcome to our Winchester Retreat! brbrCome relax at our 3-bedroom home offering a perfect escape with breathtaking views of the Shenandoah Valley. Relax in the living area, featuring two big picture windows that frame the Shenandoah Mountains. Located just a short drive from Washington, DC, and about 30 min from the Shenandoah park entrance, our home is an ideal getaway for both relaxation and exploration.brbrWith breathtaking panoramic views, charming exterior and modern interior design. This three bedroom cottage located in the heart of the Shenandoah Mountains is the perfect retreat to spend time with family or simply get away and relax. Whether you are an outdoor enthusiast, nature admirer, or beer lover, you’ll enjoy three modernly furnished bedrooms and stunning sunrises.brbr- 20 min to Eagle Rock & Tuscarora Trail in the George Washington & Jefferson National Forestbr- 20 min to Star in the Valley Vinyard and many othersbr- 20 min to Vibrissa & Box Office Breweriesbr- 35 min to Shenandoah Park Entrance
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Home Most popular vacation rentals in Winchester

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Exceptional(7)

$331.97

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

Winchester, Virginia, United States

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$105.21

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

Winchester, Virginia, United States

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$137.66

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Private vacation home

City Charmer near Historic OldTown Winchester.

Winchester, Virginia, United States

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$138.75

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Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Winchester, Virginia, United States

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$153.55

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Private vacation home

Colonial Getaway near Old Town Historic Winchester

Winchester, Virginia, United States

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$178.68

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Morocco Loft 2BR overlooking city walking mall

Winchester, Virginia, United States

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$309.90

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Country House

Modern 3BR Farmhouse in the Country

Winchester, Virginia, United States

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$156.23

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

Winchester, Virginia, United States

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$244.86

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Dog Friendly Mountain Retreat with Stunning Views

Winchester, Virginia, United States

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$165.42

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Pretty Little Apt by the Train II

Winchester, Virginia, United States

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