Destination guide

Head to the friendly city of Winchester

Learn about the unique charm of Winchester with a stay in a holiday home rental. Travellers to this welcoming city praise the restaurants, hiking and shopping. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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 cosy holiday 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 centre:

  • 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)
Natural highlights

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 centre:

  • 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)
How to get there

How to get to and around Winchester

The nearest airport is in Lexington, KY (LEX-Blue Grass), located 25.1 mi (40.5 km) from the city centre.

Where to stay near Winchester?

Our 2019 accommodation listings offer a large selection of 56 holiday rentals near Winchester. From 29 Houses to 4 Condos/Apartments, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Winchester for a long holiday or a weekend break 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 rentals for a long holiday or just a weekend break in Winchester:

  • Northside District: 39 holiday homes
  • Georgetown: 17 holiday homes
  • North Upper Street: 38 holiday homes
  • Martin Luther King: 41 holiday homes
  • Historic South Hill: 38 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes 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 homes near great places in Winchester. From HomeAway travellers, the most popular points of interest to stay near are:

  • Cassell Creek Golf Course: 150 holiday rentals
  • Southwind Golf Course: 130 holiday rentals
  • Clark Regional Medical Center: 131 holiday rentals
  • Community Park: 129 holiday rentals
  • Bluegrass Heritage Museum: 124 holiday rentals

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:

  • Condos/Apartments: 4 holiday houses
  • Cabins: 8 holiday houses
  • Cottages: 8 holiday houses

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 4 holiday homes with pool available in Winchester. Please use our search bar to access the selection of holiday rentals available.