Where to stay around Winchester?

Our 2019 accommodation listings offer a large selection of 55 holiday lettings near Winchester. From 29 Houses to 8 Bungalows, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Winchester is on HomeAway.

What is the best area to stay when travelling to Winchester?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Winchester:

  • Northside District: 45 holiday homes
  • Georgetown: 27 holiday homes
  • North Upper Street: 40 holiday homes
  • Martin Luther King: 45 holiday homes
  • Historic South Hill: 38 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Winchester?

HomeAway offers a large selection of holiday accommodations near great places in Winchester. From HomeAway travellers, the most popular points of interest to stay near are:

  • Cassell Creek Golf Course: 142 holiday lettings
  • Southwind Golf Course: 127 holiday lettings
  • Clark Regional Medical Center: 129 holiday lettings
  • Community Park: 126 holiday lettings
  • Bluegrass Heritage Museum: 121 holiday lettings

But there are many other points of interest around Winchester listed on HomeAway 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 Houses in Winchester?

Yes, of course. HomeAway offers 29 Houses in Winchester. Our other popular types of Winchester holiday rentals include:

  • Bungalows: 8 self catering accommodations
  • Cabins: 8 self catering accommodations
  • Cottages: 8 self catering accommodations

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

Can I find a holiday accommodation with pool in Winchester?

Yes, you can select your preferred holiday accommodation with pool among our 3 holiday homes with pool available in Winchester. Please use our search bar to access the selection of holiday rentals available.

    Head to the friendly city of Winchester

    Experience the unique character of Winchester with a stay in a vacation home rental. Travelers to this welcoming city praise the restaurants, hiking and shopping. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

    Activities and attractions in Winchester

    Do you want to discover attractions to visit in the city? Venture out of your cozy vacation rental and experience everything that Winchester has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

    • Southwind Golf Course (3.1 mi / 5 km)
    • Cassell Creek Golf Course (6.5 mi / 10.5 km)
    • Grimes Mill Winery (12.4 mi / 20 km)
    • Talon Winery (16.8 mi / 27.1 km)
    • Paradise Cove Aquatic Center (17 mi / 27.3 km)
    • Chrisman Mill Vineyards (21.5 mi / 34.6 km)

    Exploring the natural landscape of Winchester

    Whether you're looking for exciting outdoor activities or just want to take in the scenery, Winchester is a great place to spend some time outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

    • Lykins Park (3.1 mi / 5.1 km)
    • Community Park (3.2 mi / 5.2 km)
    • Kentucky River Museum (8.3 mi / 13.3 km)
    • Boone Station State Historic Site (11.6 mi / 18.6 km)
    • Raven Run Nature Sanctuary (14.9 mi / 24 km)
    • Jacobson Park (15.3 mi / 24.7 km)