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The Comfortable In-Towner

A cute 1 bedroom apartment located in the basement of a historic 1840s home. It has a couple small windows to let in natural light, a full-size kitchen with automatic dishwasher, fridge, big closets, Queen size memory foam bed & futon. Quiet neighborhood in Old Town Winchester, Va, two short blocks from pedestrian mall with restaurants, pubs, breweries, art galleries & lots of adorable retail shops. There is a private patio open to our courtyard with friendly neighbors and management on site.

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Nostalgia Lane 3 BR in the heart of the city

Steps from the Walking Mall this 2nd floor apartment is in a vintage Tudor style building overlooking the downtown city street. Its space is light & airy full of charm & it’s spacious-3 bedrooms will make for a fabulous stay. You can park & spend your time enjoying the local breweries the iconic John Handley Library, the Discovery Museum, delicious restaurants, galleries & shops just outside your door. Nostalgia Lane has a wonderfully peaceful relaxing vibe —You will love it ! Happy Travels!

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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!

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Downtown FUN! Personal Mid Century 2bd Apartment!

Welcome to Blossom! Your own, private pied-à-terre, located in Winchester's historic district, 1 block from the Old Town Walking Mall! Blossom's UBER-LUX upgrades include a fully-stocked custom kitchen, marble countertops, new stainless steel appliances, high speed internet, gleaming hardwood floors, queen size canopy beds, heavenly memory foam mattresses, 50' smart TV, all delivered with a Euro MCM flare! Blossom is ideal for a romantic getaway, smart business travel, or a quick City escape!

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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.

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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.

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Last Minute Deals! Luxe 2 BD Apt in OT Winchester

The Loudoun Luxe-Winchester’s Newest AirBnB just steps to the Old Town walking mall. One of the best addresses in Winchester! Don’t miss the chance to stay at this 100+ year old historic home newly renovated and customized with gorgeous hardwood flooring, quartz marbled countertops, professionally designed tile, Frigidaire/GE stainless steel appliance package (fridge, electric range, microwave, dishwasher, W/D), LED lighting, well-appointed and perfectly stocked for a fabulous holiday!

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The Flat of Old Town Winchester

This unique Flat has a style all its own. This Flat is the perfect get away! Enjoy downtown Winchester! Walk the historic walking mall and enjoy one of the great restaurants located there. This apartment has a small kitchenette with a microwave, refrigerator, coffee maker, silverware and everything you need to be comfortable. It also has electric fireplace and Tv mounted on wall. Located in the heart of Old Town Winchester. Walking distance to shops, restaurants, and entertainment.

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Cameron Grace brand new downtown 1 BR loft

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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Peaceful Family Retreat in the Heart of Winchester

Come relax in our beautiful one-room basement suite. The suite is closed off from the rest of the house so you and your family will be undisturbed. A private entrance with your own custom keycode means you can come and go as you please. Rest easy on our memory foam queen bed. The kids will enjoy the bunk bed and plenty of board games for entertainment. Roam around our quiet neighborhood or drive just a short distance to shops and entertainment. We can't wait to host you!

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Spacious Charming Basement Apt

This newly renovated space with private entrance is perfect for traveling professionals and vacation travelers alike. Close proximity to shopping and restaurants. Just off Main St (Rt 11), it is convenient to Rts 37 and 81. Less than 15 minute drive to Winchester Medical Center, Shenandoah University. Visit Local Wineries/Family Drive In Theater/ Harpers Ferry/ Skyline Drive/ Historic Winchester/ Take a day trip to DC- just 1.5 hours away. Options abound!

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The Queen of Winchester

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.

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Retro Loves Company in Old Town Winchester

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Cleveland Park bright 2BR apt blocks from downtown

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Easy like a Sunday Morning 1 BR apt great location

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Dreamweaver Bright 1BR 2 blocks to Walking Mall

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The Blue Door steps from Handley Library

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Pretty Little Apt by the Train I

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The Stock Exchange downtown hip studio apt

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Rosamond downtown studio apt w/free parking

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Yellow Submarine trendy basement apt w/courtyard

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Cozy Apartment located on our 5-acre property

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Old Town Loft In Highly Desirable Area Downtown

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The Blue Door steps from Handley Library

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Modern Twist in Old Town! Rock n' Roll FUN!

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Downtowner

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WonderClock House steps from Handley Library

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The Comfortable In-Towner

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