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WonderClock House steps from Handley Library

Come visit downtown Winchester ! You will love the WonderClock house, a vintage duplex just steps from the iconic Handley Library and the well loved pedestrian mall. Park and walk to all downtown has to offer. Two levels, three bedrooms, clawfoot tub, back staircase and three porches! Plenty of space to spread out and enjoy your time. Named after the Hosts favorite Fairytale storybook which is in the house for guests to enjoy! Any Questions: reach out to Michele Bouve Hoffman on social media

Oldtown Schoolhouse. C&O Canal Lock 70.

The space is an open concept classroom inside of an old school 500 yards from the C&0 Canal Lock 70. Guests of Lock 70 Schoolhouse enjoy the entire space of this open concept which includes 1 King Bed, 2 Bunk Beds, and a fully stocked coffee bar area with a microwave, water cooler and refrigerator and internet. A private bathroom with a hot shower awaits after your long day on the trail. Also housed in the school is a restaurant and a small store (owned by a separate party, closed on Mondays.)

Old Town 1920s Gas Station with Hot Tub

1920s Refurbished Gas Station with hot tub repurposed into a beautiful luxury apartment. Private parking/EV charging, 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, laundry and coffee nook in 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!

"Over The Ridge" Vintage Modern Apartment

"Over The Ridge" is a historic 1860's vintage modern private apartment with no one above or below you! SMOKE FREE! Located on the main route to Berkeley Springs and just minutes from Cacapon Resort State Park, this two-bedroom apartment features a separate entrance, original hardwood floors, spa-like bathroom, and curated modern design. Free parking and in-unit laundry are available. Set above a future coffee house, this stay offers history and contemporary style in one unforgettable space.

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!

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.

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.

Near I-81, but private! Laundry! No fees!

Welcome to your peaceful retreat! This spacious and clean apartment features a fully equipped kitchen, dual shower heads, a cozy living area, and a washer/dryer for your convenience. Ideal for travelers seeking a quiet getaway or a stopover along I-81, our home is close to Antietam Battlefield, Hagerstown Shopping Outlets, C&O Canal, Tomahawk MotoX, Greenbrier State Park, Shepherdstown, and Harper's Ferry. Enjoy a comfortable stay with thoughtful amenities designed to make you feel at home!

Modern 2-Bedroom Apartment/2-Bed Minutes from I-81

This modern basement apartment offers comfort and privacy. It has its own entrance for easy access, 2 private bedrooms, each with a closet, adjustable-height desk, computer chair, and TV—great for rest or remote work. The unit has 1 full bathroom with fresh towels and toiletries, a kitchenette with sink, microwave, refrigerator, and essentials for light cooking, plus a cozy living area with fireplace, TV, and fast internet. The whole unit has UltraTech-filtered water and is solar-powered.

The Speakeasy Listening Room

Step into this funky and cool haven, a spot designed for unwinding in something genuinely extraordinary! Experience the allure of secret door access leading to the listening room and bathroom, lending an air of mystery that defines "The Speakeasy." A note for visitors: a large step is required, so it's not suitable for those who may find it challenging. Enjoy the firepit and twinkling string lights on the deck. Musical souls will love the piano, guitar and record player waiting for you!

Mountain Meltdown - Pet Friendly | Wifi | Fire Pit

Sometimes, the best kind of getaway is the one that’s unassuming. Easygoing. Comfortable. Mountain Meltdown is that place—where nature sets the pace and the only thing on your to-do list is to breathe a little deeper. Tucked in a quiet spot with its own pond, campfire ring, and all the space you need, this private vacation home is perfect for families, friend groups, or couples who travel with their dogs and their sense of humor.

Kudra's Escape

Kudra's Escape is named for a character in the Tom Robbins Cult Classic - "Jitterbug Perfume." Located on the third floor, this place has the feeling of perfect light. Ideally located on Hancock's Main Street, Kudra's Escape is visible from the C&O Trail and steps from the Western Maryland Rail Trail. Walk to restaurants and the Potomac and other awesome places.