Vacation rentals in Winchester

Downtown Apartment- Renovated 1920s Gas StationBrand new refurbished gas station from 1920s repurposed into beautiful apartment. Private off-street parking with EV car charging station, full kitchen, custom shower with rain system. High speed Wi-Fi, 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, a neighborhood pizza parlor and the downtown walking mall.

Modern Upscale Home, Historic Downtown WinchesterNEW to Airbnb! Experience all the charm that downtown Winchester has to offer in this Old Town historic district home with modern flair. Just steps away from the home of country music legend Patsy Cline and a few minutes' stroll from the Winchester walking mall, the upscale style and amenities of this home can't be beat. Charming interiors, private parking, and outdoor front porch and patio spaces make this a unique find for couples, families, or groups of friends visiting the area.

Modern Elegance in Historic Old Town WinchesterJust a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.