Apartment holiday rentals in Winchester

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!

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.

Scarborough Fair walk to downtown two story apt

Come to downtown Winchester get the true feel of the city. Park & Walk to beautiful Handley Library, take a stroll to the much loved walking mall to the many shops & restaurants. Scarborough Fair is the place to enjoy the time w/family and friends. Three bedrooms, two levels, three porches, fenced yard. Eclectic & comfortable you will love your stay in this wonderful spot downtown. Looking for more space? or have any additional questions? Reach out on social media: Michele Bouve Hoffman.

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Historic District Apartment with Modern Amenities

Our apartment is located on Main Street in the Town of Mt Jackson in the beautiful Shenandoah Valley. Close to historic towns, Civil War battlefields, wineries, breweries, distilleries & hiking trails. Access to Shenandoah National Park/Skyline Drive's Thornton Gap entry is 30 miles from the Mount Jackson apartment. Shenandoah Caverns is minutes away and Luray Caverns is less than 30 minutes away. Less than 30 minutes from JMU & EMU. Easy 4 minutes access to Interstate I-81.

The Lodge at Turkey Creek

Your low tech getaway awaits in the VA Piedmont wine & hunt country! Nestled in the woods at the end of a half mile private drive you will find quiet & solitude. Your tranquil sanctuary includes a charming lower level apartment and patio. Located in the midst of expansive horse farms, charming towns, idyllic scenery, mountains and wineries.

Your own "Tiny House"

Private, furnished studio apartment. Country setting with easy access to all major highways in Frederick, MD. Convenient location for day trips to Washington, DC, Gettyburg, Harpers Ferry, Baltimore. Private bathroom. Fully furnished kitchen. Transportation can be arranged to pick up/drop off for AT and C&O Canal hikers.

Taylor Den

John Brown’s stomping grounds! Adjoining the Harpers Ferry National Historical Park, just off the Appalachian Trail and a short jaunt from Old Town Harpers Ferry - TAYLOR DEN kindly welcomes and accommodates you. Delight in nature’s magic and the whimsy of Harpers Ferry with Taylor Den as your private home base.