Compare Vacation Rentals & Airbnb in Winchester, VA

This apartment is situated in the heart of Winchester, just a short walk from the Old Town Winchester walking mall and a 5-minute drive from the Handley Library and the Museum of the Shenandoah Valley, offering easy access to the city's cultural attractions. This property has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment provides a comfortable and modern space for up to two guests, featuring a spacious living area, a well-equipped kitchen with a fridge, microwave oven, and dishwasher, and a full bathroom with a large shower. Guests can enjoy amenities such as private laundry facilities, air conditioning, free parking, and a peaceful retreat overlooking the treetops.

This Winchester city centre duplex is situated a short walk from the Handley Library and the pedestrian mall, offering easy access to the Museum of the Shenandoah Valley and Discovery Museum (less than 0.8km away).
The three-bedroom, one-bathroom apartment sleeps six, features a fairytale theme, a garden, free on-site parking, and is close to restaurants, cafes such as the Expresso Bar, and entertainment venues including the George Washington Hotel's Half Note Lounge and Bright Box.

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 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 Winchester apartment, ideally located in the Old Town district, offers easy walking access to the Handley Regional Library and Stonewall Jackson's Headquarters.
The three-bedroom, one-bathroom property includes a fully equipped kitchen with dishwasher and microwave, in-unit laundry, Wi-Fi, parking, and air conditioning, comfortably accommodating families or small groups.

This Winchester apartment offers a convenient base for exploring the city's historical attractions, situated within 1.6km of the Patsy Cline Historic House, the Shenandoah Valley Discovery Museum, and George Washington's Office.
The self-catering flat comprises one bedroom, one bathroom, sleeps two guests, and includes amenities such as Wi-Fi, parking, air conditioning, and an in-unit laundry; nearby attractions include the Bright Box Theatre and the Old Court House Civil War Museum.

This three-bedroom apartment is located on Boscawen Street in the heart of Winchester, just a short walk from the city's historic High Street and the 12th-century Winchester Cathedral.
The apartment offers a fully equipped kitchen, a spacious living area, and a private bathroom, comfortably accommodating up to six guests.

This Winchester city centre flat, a short drive (approx. 80km) from Washington, D.C. and 64km from Skyline Drive and Harpers Ferry, is situated in a historic district.
The 1-bedroom apartment, sleeping up to two guests, offers a king-size bed, queen-size sofa bed, dedicated workspace, in-unit laundry, and complimentary off-street parking, plus starter supplies.

This charming one-bedroom flat is situated on the Old Town Mall in Winchester, just a short walk from the city's historic centre and a wide range of restaurants, shops, and attractions. Guests have consistently praised the apartment's excellent location, cleanliness, and overall experience.
The flat is ideal for up to four guests and boasts a fully equipped kitchen with a fridge, freezer, and microwave oven. Enjoy the convenience of air conditioning, and explore the local craft beer scene with four breweries within walking distance.

This Old Town Winchester flat is ideally located less than 0.16 km from Winchester's historic sites, the Discovery Museum, and the Old Town walking mall, offering easy access to local attractions.
The two-bedroom, two-bathroom self-catering apartment, sleeping up to four guests, features a fully equipped kitchenette, air conditioning, and a private patio terrace.

This stylish flat is located in Old Town Winchester, just a short walk from the downtown walking mall, breweries, and the Pizzoco Pizza parlor. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The flat is a one-bedroom property with one bathroom, comfortably accommodating two guests. The apartment features a fully equipped kitchen, a private parking space with an EV charging station, and a range of modern amenities including a smart TV, high-speed Wi-Fi, and a washer/dryer.

This 2-bedroom, 1-bathroom flat is located in downtown Winchester, Virginia, 100 metres from the walking mall and within walking distance of the Shenandoah Valley Discovery Museum.
This 63 square metre apartment offers air conditioning, WiFi, a fully equipped kitchen, an in-unit washer and dryer, and a designated free parking space, accommodating up to 3 guests.

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.