Compare Vacation Rentals & Airbnb in Winchester, VA

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Winchester, VA vacation rentals
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118 Rentals and Airbnb in Winchester, VA

Best family friendly Winchester, VA vacation rentals

Among the 118 accommodations in Winchester, VA, here are the 4 best family friendly rentals

Dreamweaver  1br 1ba Just Two Blocks From The Downtown Walking Mall - Winchester, VA
8.4 6 reviews

Dreamweaver 1br 1ba Just Two Blocks From The Downtown Walking Mall

apartment, Winchester
This Winchester Historic District flat offers convenient access, within 1.6km, to Stonewall Jackson's Headquarters, the Handley Regional Library, and the Old Court House Civil War Museum.
The self-catering apartment sleeps two, features a fully equipped kitchen, free Wi-Fi, and on-request housekeeping, and is close to Bright Box Theatre and Mount Hebron Cemetery.
Downtowner - Winchester, VA
9.9 358 reviews

Downtowner

apartment, Winchester
This charming apartment is located in a quiet residential area of Winchester's Historic District, just a short walk (less than 1 km) from the bustling downtown pedestrian mall. It has consistently received excellent ratings for location, cleanliness and overall experience.
The apartment sleeps up to four guests and features a fully equipped kitchenette, a relaxing front porch, and in-house laundry facilities. Guests can enjoy a range of amenities, including free Wi-Fi, air conditioning, and private parking.
Dreamweaver Bright 1br 2 Blocks To Walking Mall - Winchester, VA
9.7 49 reviews

Dreamweaver Bright 1br 2 Blocks To Walking Mall

apartment, Winchester
This Winchester city centre flat is situated two blocks from the pedestrian mall, offering easy access to shops, restaurants, and the Handley Library.
The self-catering apartment, sleeping up to three guests, features a queen-sized bed, a futon, free on-site parking, and is close to attractions such as the Museum of the Shenandoah Valley and Skyline Drive.
Cleveland Park Bright 2br Apt Blocks From Downtown - Winchester, VA
9.5 110 reviews

Cleveland Park Bright 2br Apt Blocks From Downtown

apartment, Winchester
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.

Best Winchester, VA vacation rentals with parking

The Cozy Brick Cottage On Opequon Ave - Winchester, VA
8.0 1 review

The Cozy Brick Cottage On Opequon Ave

apartment, Winchester
This three-bedroom, one-bathroom flat is located in Winchester, just 5 minutes from Old Town and 20 minutes from Shenandoah hikes and wineries.
This pet-friendly accommodation offers parking, air conditioning, and a fully equipped kitchen, with a guest capacity of six.
Newly Repurposed Historic Home In Winchester Va! - Winchester, VA
9.8 144 reviews

Newly Repurposed Historic Home In Winchester Va!

apartment, Winchester
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.
Merrimans Hope 5br Spacious & Stunning - Winchester, VA
10 2 reviews

Merrimans Hope 5br Spacious & Stunning

apartment, Winchester
This five-bedroom, two-bathroom holiday home in Winchester offers convenient access to nature and culture, located a 2-minute drive from Abrams Creek Wetlands Preserve and the Museum of the Shenandoah Valley.
This spacious 539 square meter property accommodates up to 10 guests and features Wi-Fi, air conditioning, a garden, and on-site parking.
Cameron Loft 2 Story Studio With 1.5 Bath Downtown - Winchester, VA
10 17 reviews

Cameron Loft 2 Story Studio With 1.5 Bath Downtown

apartment, Winchester
The Cameron Loft, a two-level studio apartment in Winchester city centre, offers convenient access to downtown attractions.
This self-contained apartment sleeps two, features a fully equipped kitchen, in-unit laundry, complimentary parking, and fast WiFi; starter supplies are provided.

Frequently Asked Questions about vacation rentals in Winchester, VA

  • What are the top family-friendly attractions in Winchester, VA?

    The Jim Barnett Park is a great spot for families, with a playground, picnic areas, and a walking trail. The Winchester Apple Festival, held in September, is also a fun family event with live music, food, and activities for all ages. And the Frederick County Fairgrounds, with its annual fair, is another great option for family fun.
  • What are the best Airbnb and vacation rentals in Winchester, VA?

    Immerse Yourself In Old Town Winchester (Apt #4), City Charmer Near Historic Oldtown Winchester and Downtown 1920's Gas Station With Hot Tub are the most popular Airbnb and vacation rentals in Winchester, VA among travelers.

  • When is the best time to book a vacation rental in Winchester, VA?

    You'll want to book well in advance if you're planning to visit during peak season, which is typically from May to October. You'll find better deals if you book outside of these months, but you might miss some of the popular events.
  • What are the most popular Airbnbs in Winchester, VA?

  • What events or festivals should visitors check out in and around Winchester, VA?

    The Apple Blossom Festival in April is a big one, with parades, concerts, and lots of food stalls. The Winchester Wine & Food Festival in September is another popular event, featuring local wines and food.
  • What are the best rentals for families and kids in Winchester, VA?

  • What are the best budget-friendly activities in Winchester, VA?

    You can easily spend a day exploring the Old Town on foot, popping into the shops and admiring the architecture. The Winchester Public Library is free to visit and has a great selection of books and events.
  • What are the best rentals or Airbnbs with a jacuzzi in Winchester, VA?

    The best vacation rentals or Airbnb with a jacuzzi in Winchester, VA are Downtown 1920's Gas Station With Hot Tub, Charming Family Luxury Home and Cozy Beautiful House.

  • What are the best restaurants with local dishes in Winchester, VA?

    For a taste of local cuisine, try The Winchester Brew Works for their craft beers and pub grub. The Red Rooster Restaurant is another popular spot, known for their southern comfort food.
  • What are the best walking or cycling routes in Winchester, VA?

    The Apple Orchard Trail is a great option for a leisurely walk or bike ride, with beautiful scenery and plenty of places to stop for a break. The Shenandoah River Trail is also a popular choice, offering stunning views of the river.
  • Are there pet-friendly attractions in Winchester, VA?

    The Jim Barnett Park is a great option for a walk with your dog, with a designated off-leash area. Many of the restaurants in the Old Town also welcome well-behaved dogs on their patios.
  • What are the benefits of choosing a vacation rental in Winchester, VA?

    Vacation rentals offer more space and privacy than a hotel room, and often come with amenities like a kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Winchester, VA?

    The Winchester Sports Complex is a great spot for sporting events, with fields for baseball, softball, soccer, and more. The James Wood High School also has a variety of sports facilities, including a football stadium, track, and tennis courts. And the Winchester YMCA offers a variety of fitness classes and programs.

Popular destinations

Best Winchester, VA vacation rentals with a balcony

Queen Of Winchester - Three Bedroom Apartment - Winchester, VA
9.6 64 reviews

Queen Of Winchester - Three Bedroom Apartment

apartment, Winchester
This three-bedroom Winchester apartment, named 'Queen of Winchester', enjoys a central location offering easy access to Winchester's historic city centre and its numerous attractions, including Winchester Cathedral.
The luxurious flat features a private terrace, parking, air conditioning, and internet access, comfortably sleeping four guests.

Best pet friendly Winchester, VA vacation rentals

Among the 118 accommodations in Winchester, VA, here are the 3 best pet friendly rentals

Treasure House - Winchester, VA
9.7 12 reviews

Treasure House

apartment, Winchester
This three-bedroom Winchester house, sleeping seven, is located a short 3.2-kilometre drive from Winchester city centre, offering easy access to restaurants and the Winchester Shopping Centre.
The property boasts a fully equipped eat-in kitchen, designated workspace, high-speed internet, ample parking, and is pet-friendly (dogs welcome), providing a comfortable stay for families or groups visiting Winchester.
Morocco Loft 2br Overlooking The City - Winchester, VA
9.5 64 reviews

Morocco Loft 2br Overlooking The City

apartment, Winchester
This charming apartment is situated in the heart of Winchester, just a stone's throw from the bustling walking mall, the fascinating Discovery Museum, and a plethora of shops and restaurants. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers two bedrooms, a small office area, and a dining area with a sofa bed, comfortably accommodating up to five guests. It includes a fully equipped kitchen, a bathroom with laundry facilities, and air conditioning, making it ideal for both short and long stays.
Winchester Farm - Winchester, VA
10 13 reviews

Winchester Farm

apartment, Winchester
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.
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