Destination guide

Charming Winchester will entice you

The lake and other outdoor surroundings create an inviting atmosphere in Winchester. Revered for its theme park, boating and university setting, this city is both romantic and welcoming. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.


Activities and attractions in and around Winchester

Are you hoping to discover top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winchester a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Sewanee Golf and Tennis Club (12.9 mi / 20.7 km)
  • Fayetteville Golf and Country (25 mi / 40.2 km)
Natural highlights

Exploring the natural features in Winchester

Whether you're an active traveller or just want to spend some time taking in the scenery, Winchester is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Cheston (12 mi / 19.3 km)
  • Great Stage Park (20.5 mi / 33 km)
  • Russell Cave National Monument (23.3 mi / 37.5 km)
How to get there

Travelling to and around Winchester

The nearest airport is in Huntsville, AL (HSV-Huntsville Intl.), located 51.6 mi (83 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Chattanooga, TN (CHA-Chattanooga Metropolitan), which is 54.3 mi (87.4 km) away.

How many holiday accommodation are available around Winchester?

Our 2020 accommodation listings offer a large selection of 92 holiday rentals around Winchester. From 60 Houses to 22 Cabins, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Winchester is on Stayz.

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

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

  • Expressions: 96 holiday rentals
  • Hammers: 94 holiday rentals
  • Tim's Ford Marina: 73 holiday rentals
  • Tims Ford State Park: 72 holiday rentals
  • Jack Daniel's Distillery: 69 holiday rentals

But there are many other points of interest around Winchester listed on Stayz 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. Stayz offers 60 Houses in Winchester. Our other popular types of Winchester holiday rentals include:

  • Cabins: 22 holiday houses
  • Cottages: 22 holiday houses
  • Bungalows: 22 holiday houses

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

Can I find a holiday accommodation with pool in Winchester?

Yes, you can select your preferred holiday accommodation with pool among our 18 holiday homes with pool available in Winchester. Please use our search bar to access the selection of holiday rentals available.