Destination guide

Charming Winchester will entice you

The lake and other outdoor surroundings create an inviting atmosphere in Winchester. Well-liked for its theme park, boating and university setting, this city is both romantic and welcoming. If you're looking for accommodations 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 vacation rental, you'll want to experience everything that makes Winchester a fun spot to vacation. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

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

Exploring the natural features in Winchester

Whether you're an active traveler 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 center:

  • 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

Traveling to and around Winchester

The nearest airport is in Huntsville, AL (HSV-Huntsville Intl.), located 51.6 mi (83 km) from the city center. 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.

Where to stay near Winchester?

Our 2019 vacation rental listings offer a large selection of 85 house rentals near Winchester. From 54 Houses to 23 Cabins, find unique vacation rental 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 are the popular points of interest near where I can stay when travelling to Winchester?

HomeAway offers a large selection of lodging choices near lovely places in Winchester. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Tims Ford State Park: 69 home rentals
  • Jack Daniel's Distillery: 67 home rentals
  • George Dickel Distillery: 70 home rentals
  • Great Stage Park: 34 home rentals
  • University of the South: 80 home 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 vacation rentals available near the point of interest of your choice.

Can I rent Houses in Winchester?

Yes, of course. HomeAway has 54 Houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Cabins: 23 lodging choices
  • Cottages: 23 lodging choices
  • Bungalows: 23 lodging choices

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

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 16 vacation homes with pool available in Winchester.