House holiday rentals in Winchester

Arden House, Inwood WV

Ground level two room unit. No steps. Separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed, sofa and full refrig.. In a separate living area, there is a queen bed, TV, bathroom, desk, table, microwave, convection oven, air fryer, gas fireplace. No oven. Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic

Cozy Reliance Retreat with Beautiful Views

Welcome to the Reliance Retreat in the heart of the Shenandoah Valley! Our luxurious space is inviting and tranquil. Whether you're just passing through or need some peace and quiet away from the city, this cozy house has an amazing mountain view we know you'll enjoy. The house sleeps four and includes all the amenities you'll need in every area of the home. We hope you'll grab a book, your favorite snacks and find yourself a cozy spot whether it's inside, on the patio, or out by the fire pit

Lindas Country Cottage

Come and relax in our Little County Charmer If needed for extended t. Under 2 miles from Interstate. 15 min from Charlestown Casino and horse racing. JD’s Fun Center with pool for children. ..2 hrs from Massanuttan . Take a ride to Historic Berkley Springs Or Harpers ferry.. Home is in a quite neighborhood. Tv Wi-Fi. Home is close to dining and fast foods delivery. So if you wanna feel right at home while visiting or town stop by and pay a visit at our small home with a little country charm

Jay Birds Nest - Pet Friendly

Welcome to Jay Birds nest, located in the historic town of Edinburg, Virginia. Just 1.5 miles from I-81. Fully equipped with all the comforts of home and gorgeous mountain views. Enjoy having the entire house to yourself with sleeping for 6 with 2 queen bedrooms and 1 full bedroom and one full bath. Plenty of parking with room for two cars, one under a car port. Have your morning coffee in the relaxing sunroom or in the outdoor seating area. Just a quick walk away from the Shenandoah River.

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

Historic District Charm On Cameron Street

Charming home located in the historic district of Winchester. A short walk to the walking mall,restaurants, shopping, farmer's markets,breweries and more. Convenient to Shenandoah University, Winchester Medical Center, many museums including the Museum of the Shenandoah Valley, George Washington Hotel, Skyline Drive, 81 and more. Big deck and a half court basketball in the back yard. We have added a work/office area with a desk and chair ideal for working or schooling from home.

The Cozy Cottage-2 mins to I-81

Kick back and relax in this calm, stylish cottage. Welcome to "The Cozy Cottage". Escape the mundane and embark on outdoor adventures like fishing, hiking, rock climbing, zip-lining, history, wineries, breweries, antiquing and more from this vacation Cozy Cottage just 2 miles from I-81. We are located in Edinburg, Virginia. This 2-bedroom, 1-bathroom house offers all the modern amenities of home in a cottage-inspired living space.

Little Red Schoolhouse in Cross Junction

Step into our charming red schoolhouse—your cozy, vintage-inspired 1BR retreat! Enjoy a unique stay with modern comforts, nostalgic décor, and sun-filled spaces. Perfect for romantic getaways or peaceful escapes. High ceilings, natural light, and warm wood floors set the scene. Just minutes from scenic hikes, wineries, and local attractions. Book your unforgettable Airbnb experience now in this one-of-a-kind historic stay!

Aunt Tim's Farmhouse

Our farmhouse is located approximately 5 miles west of Historic Winchester, VA. The house is situated on 106 acres of an operational farm. You may see family members and friends tending honey bee hives, working in the detached garage, gardening, and completing other farm chores. The house is solely occupied by our guests. Come on out to enjoy some peace and quiet and take advantage of all Mother Nature has to offer!