Discover a selection of 268 holiday rentals in Winchester that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 39 per night, and cabins and houses are popular options for a stay in Winchester. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Winchester
Destination guide

Head to the historical city of Winchester

Come and experience Winchester and its history, theatre scene and entertainment. Well known for its shopping, restaurants and university setting, this welcoming city won't disappoint. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.


Sightseeing in and around Winchester

Are you looking for things to do while you're in town? Venture out of your holiday home and check out everything that makes Winchester a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Rock Harbor Golf Course (2.2 mi / 3.5 km)
  • Wilson's Wild Animal Park (5.7 mi / 9.3 km)
  • Appleland Sports Center (5.9 mi / 9.5 km)
  • Valerie Hill Winery (8.6 mi / 13.8 km)
  • Dinosaur Land (8.7 mi / 14 km)
  • Rocking S Ranch (8.9 mi / 14.3 km)
Natural features

Exploring the natural landscape of Winchester

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Winchester. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Jim Barnett Park (1 mi / 1.6 km)
  • State Arboretum of Virginia (10 mi / 16.1 km)
  • Cedar Creek and Belle Grove National Historical Park (13.4 mi / 21.6 km)
  • Hupp's Hill Civil War Park (16.1 mi / 25.9 km)
  • Front Royal Entrance Shenandoah National Park (19.3 mi / 31 km)
  • Skyline Caverns (19.8 mi / 31.8 km)
How to get there

How to get to and around Winchester

The nearest airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Washington, DC (IAD-Washington Dulles Intl.), which is 41.7 mi (67.1 km) away.

Can I find a vacation rental around Winchester?

Yes, our 2021 property listings offer a large selection of 268 vacation rentals near Winchester. From 62 cabins to 216 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winchester for a holiday or a weekend are on Vrbo.