Compare Vacation Rentals & Airbnb in Winchester, VA

118 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Winchester, VA vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

118 Rentals and Airbnb in Winchester, VA

Best family friendly Winchester, VA vacation rentals

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

New Charming 3-bedroom  2 Full Bath And 1 Half Bedrooms Single Family  House - Winchester, VA
8.6 10 reviews

New Charming 3-bedroom 2 Full Bath And 1 Half Bedrooms Single Family House

apartment, Winchester
This Winchester townhome, near Red Bud Run and Jim Barnett Park, offers easy access to the Shenandoah Valley Discovery Museum and Nalls Farm Market.
Sleeping up to 30 guests, this three-bedroom, four-bathroom property includes a king, queen, and full-size bed, an office with a futon, in-unit laundry, WiFi, air conditioning, and parking, making it ideal for large groups visiting Winchester.
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.
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.

Best Winchester, VA vacation rentals with parking

Nostalgia Lane 3 Br In The Heart Of The City - Winchester, VA
9.7 241 reviews

Nostalgia Lane 3 Br In The Heart Of The City

apartment, Winchester
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.
Cameron Street Retreat: King Bed & Office Downtown - Winchester, VA
9.8 26 reviews

Cameron Street Retreat: King Bed & Office Downtown

apartment, Winchester
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.
Old Town Modern Twist! Rock N Roll Fun W/parking! - Winchester, VA
9.9 208 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.

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

House/cottage 2bed, Private Yard, Walk To Oldtown - Winchester, VA
9.8 48 reviews

House/cottage 2bed, Private Yard, Walk To Oldtown

house, Winchester
This charming cottage is situated just 3 kilometres from Winchester Medical Centre and a short walk from the town centre, offering a peaceful escape from the hustle and bustle. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The cottage provides a comfortable and private space for two guests, with a fully equipped kitchen and a relaxing garden. Enjoy the convenience of self check-in, air conditioning, and a cosy fire pit for evening relaxation.

Best pet friendly Winchester, VA vacation rentals

Among the 118 accommodations in Winchester, VA, here are the 4 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.
The Blue Door Steps From Handley Library - Winchester, VA
9.5 116 reviews

The Blue Door Steps From Handley Library

apartment, Winchester
This Winchester city centre studio apartment is conveniently located near the Handley Library, two blocks from the pedestrian shopping area, and within an 8km drive of Shenandoah University and Winchester Medical Centre.
The self-catering apartment sleeps two, boasts a full kitchen with fridge and microwave, a 32” flat-screen TV with Roku, two complimentary parking spaces, and access to on-site laundry facilities; nearby attractions include the Skyline Drive (a 48km drive) and Washington, D.C. (a 240km drive).
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.
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.
©2026 cozycozy.com