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.

How many vacation rentals are available around Winchester, TN?

Our 2020 property listings offer a large selection of 91 vacation rentals around Winchester. From 21 cabin rentals to 60 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Winchester?

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

  • Tims Ford State Park: 72 vacation rentals
  • Tim's Ford Marina: 73 vacation rentals
  • Hammers: 93 vacation rentals
  • Monteagle Sunday School Assembly: 84 vacation rentals
  • University of the South: 95 vacation rentals

But there are many other points of interest around Winchester listed on Vrbo 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 Cabins in Winchester?

Yes, of course. Vrbo has 21 Cabins in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Houses: 60 rentals available
  • Cottages: 21 rentals available
  • Bungalows: 21 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Winchester?

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