Search All Cottages in Winchester, VA

Find the best offers in Winchester, VA

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Winchester, VA cottages
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Winchester, VA Cottages: no available offers. Here are other great options for your stay!

Secret Gardens Tiny House - Winchester, VA
10 49 reviews
Winchester, VA
27/07 – 03/08
£84/nighttotal: £588 (7 )

Secret Gardens Tiny House

1 2
cabin , Winchester
This Winchester self-catering cottage is situated a 5-minute drive (8 km) from Winchester's Old Town walking mall and 30 minutes (48 km) from the Blue Ridge Mountains, offering easy access to Shenandoah Valley attractions.
The 1-bedroom, 1-bathroom property sleeps 2 guests and features a queen-size bed in a loft, laundry facilities, a private patio overlooking a zen garden, a fire pit, and access to organic vegetable/herb gardens.
King + Sofa Bed L George Washington L Downtown - Winchester, VA
Winchester, VA
06/07 – 07/07
£140/nightfor 1 night

King + Sofa Bed L George Washington L Downtown

1 2
B&B , Winchester
This guest house in Winchester, located within the Shenandoah Valley, is situated in the city centre, offering straightforward access to local points of interest.
The stylish accommodation provides a 30.8 square meter room with a king bed and sofa bed for two guests, featuring air conditioning, Wi-Fi, a shared indoor heated pool, fitness centre access, and paid valet parking at £12 per day, with daily cooked-to-order breakfast available for an extra charge.
Modern Hotel With Small Town Charm - Winchester, VA
9.3 76 reviews
Winchester, VA
18/10 – 24/10
£124/nighttotal: £744 (6 )

Modern Hotel With Small Town Charm

1 4
B&B , Winchester
This Winchester guest house enjoys a prime location in the Shenandoah Valley, a short walk from Shenandoah University and within easy driving distance (approximately 48km) of Skyline Drive and the Blue Ridge Parkway.
The self-catering property features one bedroom, one bathroom, sleeps four guests, and offers amenities including air conditioning, Wi-Fi, parking, and a swimming pool; pets are welcome.
Private Studio Space - Winchester, VA
9.8 10 reviews
Winchester, VA
27/07 – 03/08
£67/nighttotal: £469 (7 )

Private Studio Space

1 2
B&B , Winchester
This studio apartment is located in the heart of Winchester, just a short walk from the city's historic landmarks like Winchester Cathedral and the Great Hall. The surrounding area is bustling with shops, restaurants, and pubs, offering a lively atmosphere. The studio has received excellent ratings for cleanliness, location, and user experience.
The apartment features a comfortable living space, perfect for two guests. It comes equipped with a kitchen, air conditioning, and a private garden, making it an ideal base for exploring Winchester and its surrounding countryside.

Frequently asked questions about cottages in Winchester, VA

  • What part of Winchester, VA is ideal for renting a cottage?

    The Apple Pie Ridge area, located just outside Winchester, is popular for renting cottages. It's a peaceful and scenic area with rolling hills and beautiful views. You'll find a good selection of cottages with various amenities there.
  • What are the best cottages in Winchester, VA?

  • When is the best time to rent a cottage in Winchester, VA?

    The best time to rent a cottage in Winchester is during the spring or autumn. The weather is mild and pleasant, and the scenery is stunning. You can enjoy outdoor activities like hiking and biking without the summer heat or winter chills.
  • What are the best cottages with a jacuzzi in Winchester, VA?

  • What are the can't-miss sights in Winchester, VA?

    You definitely shouldn't miss the Winchester-Frederick County Historical Society Museum, the Handley Library, and the Old Court House. They offer a glimpse into the rich history of the city. Also, don't forget to explore the Winchester and Frederick County Visitors Center for more information and tips.
  • What are the best cottages for families and kids in Winchester, VA?

    The best cottage for families and kids in Winchester, VA is Cottage Close To Old Town Winchester.

  • Why consider renting a cottage in Winchester, VA for your stay?

    Renting a cottage in Winchester offers a more relaxed and private experience compared to staying in a hotel. You'll have more space, often with amenities like a kitchen and laundry facilities, and the chance to enjoy a peaceful setting.
  • What are the best pet friendly cottages in Winchester, VA?

    The best pet friendly cottage in Winchester, VA is Cottage Close To Old Town Winchester.

  • Can you easily explore Winchester, VA on foot or by bike?

    Yes, Winchester is quite walkable, especially the historic Old Town area. You can easily explore the main attractions on foot, and there are also bike paths available for longer journeys. You can rent bikes at several places in the city.
  • What are the best cottages with parking in Winchester, VA?

  • What are the best restaurants in Winchester, VA with nature views?

    The Red Rooster Restaurant on the outskirts of town offers beautiful views of the surrounding countryside. The Winchester Brew Works has a patio overlooking the Shenandoah River, which is perfect for enjoying a meal and a drink on a sunny day.
  • What family-friendly activities are available in Winchester, VA?

    Winchester has plenty to offer families. The Jim Barnett Park offers a playground, picnic areas, and walking trails. The Frederick County Fairgrounds hosts various events throughout the year, including the annual Frederick County Fair, which is a great family day out.

Destinations nearby

©2026 cozycozy.com