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.

How many holiday rentals are available around Winchester?

Our 2020 accommodation listings offer a large selection of 217 holiday lettings around Winchester. From 52 cabins to 52 cottages, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Winchester? offers a large selection of holiday accommodations near great places in Winchester. From travellers, the most popular points of interest to stay near are:

  • Winchester Medical Center: 58 holiday lettings
  • Wilson's Wild Animal Park: 92 holiday lettings
  • Winchester Little Theater: 61 holiday lettings
  • Abram's Delight: 75 holiday lettings
  • The Kernstown Battlefield: 63 holiday lettings

But there are many other points of interest around Winchester listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Cabins in Winchester?

Yes, of course. offers 52 Cabins in Winchester. Our other popular types of Winchester holiday rentals include:

  • Cottages: 52 self catering accommodations
  • Houses: 97 self catering accommodations
  • Flats: 24 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Bungalows and more.

Can I find a holiday accommodation with pool in Winchester?

Yes, you can select your preferred holiday accommodation with pool among our 31 holiday homes with pool available in Winchester. Please use our search bar to access the selection of holiday rentals available.