House holiday rentals in Winchester

Hart's Overlook | Hot Tub, Stunning Mtn Views+Pond

BNB Breeze Presents: Hart's Overlook! Experience the West Virginia Mountains from our newly built retreat! With a private hot tub, fire pit, and picturesque views of the West Virginia Mountains, you'll have your personal retreat in paradise! This newly built modern cabin includes: - Hot Tub overlooking the Stunning Views. - Fire Pit w/ wood provided for you. - Smart TV - Charcoal Grill (charcoal provided) - Hilltop Pavilion - Private Pond - Picturesque Views oh yeah we said that already :

Location · Value · Check-in

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

Family · Value · Amenities

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Value · Family · Quiet

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 two 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

Value · Location · Pets

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fish~Swim

Mountain home: like in the movies, on 50 acres. Includes soaring mountain views, swimming holes, hiking trails, ATV trails, fishing creek, mini white sand beach, hot tub in a cave, huge boulder rustic fire pits, cave, lake, cabanas, all in a heavy forest exclusively for guests. Private: you cannot see another house from the front porch or back decks and it has thick woods all around. At the top of the property are soaring views with 3 miles of visibility. No need to go to the national park.

Family · Location · Check-in

Cedar Creek Wayside Castle

1930 Stone House 'Mini Castle' on 9 private acres near Strasburg Virginia bordering Cedar Creek Battlefield and Belle Grove Plantation National Park. Home was built by Otis Elevator company in 1930 for their daughter. You have nature trails and fire pit, swimming pool (opened April 15th), deer and wildlife too. Short walk to historic Ceder Creek. Full estate is yours to play and relax. No dogs in pool. Pool is open early April to early October usually. Hot tub is ready year round.

Location · Value · Access

Colonial Getaway Near Old Town Historic Winchester

Colonial style home- enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms and 2.5 bathrooms. Perfect for a family or a longer stay. Just a few miles drive to Old Town Winchester which includes numerous restaurants, bars, shopping and some kind of event... like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. Near by to other scenic attractions as well- Shenandoah National Park, Luray Caverns, and Harper's Ferry!

Value · Location · Sleep quality

Gorgeous cabin on Blue Ridge

Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

Family · Location · Bathroom

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!

Value · Location · Long stay

Windy Knoll Adventure | River Front | Hot Tub!

Discover our Black Modern Charm Home, a private retreat atop 35 acres with sweeping mountain and Shenandoah River views. Relax in the hot tub overlooking the river, fish or kayak below, and unwind by the campfire in this peaceful woodland setting. 🌲♨️ Designed for comfort and escape, this modern retreat is perfect for unplugging, reconnecting, and enjoying nature at its finest. Book now for a true mountaintop getaway. ✨

Family · Location · Wi-Fi

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!

Location · Family · Bathroom

Bryce Resort Chalet | Amazing Views | Sleeps 10

Discover the perfect mountain retreat at Bryce Resort! Our award winning home offers breathtaking mountain views, a 5-minute walk to ski lifts, and a short drive to golf, hiking, and Lake Laura. With 5 bedrooms, 3 baths, a large fireplace, 2 spacious decks, and high-speed WiFi, it’s ideal for families, groups, and remote work. Enjoy skiing, biking, kayaking, or lounging by the fire—book your stay today!

Family · Value · Access