Compare Vacation Rentals & Airbnb in Winchester, VA

This Winchester city centre apartment is located opposite the John Handley Library and a short 0.16 km walk from the Old Town Walking Mall.
The fully renovated loft sleeps seven guests in one bedroom with a king-size bed, a queen bed, two twin beds, and a sofa bed, offering free on-site parking, a fully equipped kitchen, and access to a sun porch.

This Winchester apartment is ideally located in the heart of the city, just a short walk from the Handley Library, the walking mall, and the Scarborough Fair, making it easy to explore the area's historical attractions and vibrant atmosphere. It has received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
This spacious home offers three bedrooms and can comfortably accommodate up to eight guests. It features a fully equipped kitchen, air conditioning, a garden, and multiple porches for relaxing, as well as free parking and pet-friendly policies.

This recently renovated 1930s house, located in Winchester, Virginia's up-and-coming downtown area, is a 5-minute walk from the Old Town walking mall and within easy reach of Shenandoah University (8 km), Winchester Medical Center (16 km), and Skyline Drive (48 km).
This 150 sq m property offers two master suites each with an en-suite bathroom and walk-in closets, a dine-in kitchen with fridge, microwave, and dishwasher, accommodating up to four guests and boasting a garden and parking.

This two-bedroom flat is located in Cleveland Park, just 0.2km from the walking mall in Winchester's downtown area, making it ideal for exploring the city's shops, restaurants, and cultural attractions. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The ground floor flat sleeps up to five guests and features a fully equipped kitchen with a fridge and microwave, air conditioning, and designated parking. Guests can enjoy the spacious living room with a sofa bed, as well as the convenience of internet access and pet-friendly policies.

This Winchester apartment is conveniently located within 1.6km of the Winchester Little Theatre, George Washington's Office, and the Shenandoah Valley Discovery Museum.
The one-bedroom, one-bathroom flat sleeps two guests and includes in-unit laundry facilities, free Wi-Fi, and essential amenities such as a TV, hairdryer, and iron; nearby attractions include the Bright Box Theatre and the Old Court House Civil War Museum.

This Winchester basement flat offers a private suite with keycode access, situated in a quiet neighbourhood a short drive from local shops and entertainment.
The self-contained apartment sleeps four, featuring a queen-size memory foam bed and bunk beds, a full bathroom, and board games; responsive hosts ensure a comfortable stay.

This charming apartment is situated just a short distance from Old Town Winchester's walking mall, offering easy access to the town's shops, restaurants, and cultural attractions. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment is a one-bedroom property that can comfortably accommodate two guests. It features a private patio, a modern kitchen, a washer and dryer, high-speed internet, and a 50-inch smart TV. Guests can enjoy the convenience of a pet-friendly environment, a garden, and the unique charm of a historic 1790s structure.

This ground-floor flat is situated in the Winchester Historic District, offering convenient access to downtown shops, the walking mall, Bright Box Theater, and the Old Court House Civil War Museum, all within a 500-meter walk.
This 2-bedroom, 1-bathroom apartment accommodates up to 5 guests and features air conditioning, parking, and a kitchen with a microwave oven, providing easy access to Abrams Creek Wetlands Preserve and Red Bud Run.

This Winchester city centre apartment is situated a 1.5-block walk from the Winchester City Mill, offering easy access to the Saturday Farmers' Market and shops.
The self-contained studio flat, sleeping up to two guests, features a full-size futon, kitchen with fridge and microwave, air conditioning, on-site parking, and a large flat-screen TV; coin-operated laundry facilities are available on the ground floor.

This Stephens City apartment, situated in the Shenandoah Valley, is approximately 16km from Winchester, Virginia, and 160km from Washington, D.C. and Luray Caverns.
The two-bedroom, two-bathroom property sleeps four guests and includes amenities such as Wi-Fi, parking, and air conditioning; nearby attractions include a lake, nature trail, and local library.

This two-bedroom flat is situated in the heart of Winchester, just a stone's throw from the Handley Library and the bustling walking mall. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment comfortably accommodates up to four guests and features a queen-sized bed in one bedroom and a double futon/couch in the other. Guests can enjoy amenities such as air conditioning, a garden, parking, and a shared laundry room, making it ideal for a relaxing and convenient stay.

This Winchester farmhouse, sleeping six guests across three bedrooms and two bathrooms, is situated [Insert precise location within Winchester, e.g., near the city centre, 5km from Winchester Cathedral, or specify a district and distance to a landmark].
The self-catering property boasts a swimming pool, fitness centre, and ample parking, along with WiFi and air conditioning, perfect for families seeking a relaxing country escape near Winchester.

This Old Town Winchester flat offers a convenient location, less than 1 km from the Handley Regional Library, Old Courthouse Civil War Museum, and Bright Box Theatre.
The 209 square metre self-catering property sleeps up to 10 guests and includes three bedrooms, one bathroom, in-unit laundry, a fireplace, and a Smart TV, plus parking.