Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Rental unit in Winchester

Downtown Renovated 1920's Gas Station

Brand new refurbished gas station from 1920's repurposed into beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

SUPERHOST

Cottage in Winchester

Springtime Cottage Escape! Hot Tub*Privacy*Views!

Disentangle and Unwind at Foxy, your exclusive cottage retreat 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 yourself in luxury and 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...

Individual Host

SUPERHOST

Rental unit in Winchester

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.

Professional Host