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 2 best family friendly rentals

Whole 3-bedroom House Walkable To Downtown. - Winchester, VA
9.9 38 reviews

Whole 3-bedroom House Walkable To Downtown.

apartment, Winchester
Nancy's Nook, a three-bedroom house in a quiet Winchester neighbourhood, is within easy walking distance of the Old Town's Walking Mall and farmers market.
This single-storey property sleeps six, boasts two sitting rooms, a sunroom, high-speed internet, and off-street parking for two cars, plus nearby amenities including Walmart, Target, and Martins Grocery.
Dreamweaver  1br 1ba Just Two Blocks From The Downtown Walking Mall - Winchester, VA
8.8 5 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.

Best Winchester, VA vacation rentals with parking

Very Charming & Spacious 2 Bedrm - Winchester, VA
8.0 1 review

Very Charming & Spacious 2 Bedrm

apartment, Winchester
This Winchester apartment is situated near the Apple Blossom Mall (8 km) and Patsy Cline's childhood home (9.6 km), offering easy access to the Shenandoah River and Mackintosh Fruit Farm.
The two-bedroom, one-bathroom flat provides internet, air conditioning, and in-unit amenities including towels and hairdryer; nearby attractions include the Shenandoah Valley Museum and Nalls Farm Market.
Old Town Modern Twist! Rock N Roll Fun W/parking! - Winchester, VA
9.9 203 reviews

Old Town Modern Twist! Rock N Roll Fun W/parking!

apartment, Winchester
This charming flat is situated in the heart of Winchester, just a short walk from the city's bustling coffee shops, restaurants and boutiques, as well as the historic Shenandoah Valley Museum. It has received excellent ratings for location, cleanliness and overall experience.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. It includes a fully equipped kitchen, a dedicated workspace, a private parking space, a washer and dryer, and air conditioning for a comfortable stay.
Secret Gardens Carriage House - Winchester, VA
9.7 93 reviews

Secret Gardens Carriage House

apartment, Winchester
This charming carriage house is located in Winchester, Virginia, a 5-minute drive from the Old Town Walking Mall and 30 minutes from the Blue Ridge Mountains. The property has received excellent ratings for location, cleanliness and overall experience.
This self-catering property can accommodate up to two guests and features a private screened-in porch, a fire pit, and a garden where you can pick fresh herbs. Guests can also enjoy the tranquil Zen gardens, observe local wildlife, and benefit from the expertise of the owners, Ramana and John.
Merrimans Hope 5br Spacious & Stunning - Winchester, VA
10 1 review

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.

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

191 M² House ∙ 3 Bedrooms ∙ 6 Guests - Winchester, VA
No reviews

191 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Winchester
House rental for 6 people. You will be based in Winchester.
Facilities and services: a kitchen, a fridge and a freeze. Take advantage of the garden in this house in Winchester.

Best pet friendly Winchester, VA vacation rentals

Among the 118 accommodations in Winchester, VA, here are the 1 best pet friendly rentals

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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