Destination guide

Head to the friendly city of Winchester

Experience the unique character of Winchester with a stay in a vacation home rental. Travelers to this welcoming city praise the restaurants, hiking and shopping. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation 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 cozy vacation 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 center:

  • 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 features

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 center:

  • 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 center.

Can I find a vacation rental around Winchester?

Yes, our 2019 property listings offer a large selection of 65 vacation rentals near Winchester. From 30 Houses to 8 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winchester for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Winchester?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winchester:

  • Historic South Hill: 41 vacation rentals
  • Northside District: 47 vacation rentals
  • Woodward Heights: 36 vacation rentals
  • Georgetown: 19 vacation rentals
  • North Upper Street: 45 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Winchester?

HomeAway offers a large selection of vacation rentals 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:

  • Bluegrass Heritage Museum: 143 vacation rentals
  • Clark Regional Medical Center: 153 vacation rentals
  • Community Park: 149 vacation rentals
  • Cassell Creek Golf Course: 175 vacation rentals
  • Southwind Golf Course: 153 vacation 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 30 Houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Condos/Apartments: 8 rentals available
  • Cabins: 9 rentals available
  • Cottages: 9 rentals available

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

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 2 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.