Discover a selection of 104 vacation rentals in Winchester that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $202 per night, and cabins and houses are popular options for a stay in Winchester. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Winchester
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, Vrbo 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?

Our 2021 property listings offer a large selection of 104 vacation rentals around Winchester. From 19 cabin rentals to 96 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.