Where to stay around Winchester, KY?

Our 2018 property listings offer a large selection of 13 vacation rentals near Winchester. From 4 cottages to 3 cabins, 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 VRBO.

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:

  • Georgetown: 24 vacation rentals
  • Northside District: 42 vacation rentals
  • North Upper Street: 38 vacation rentals
  • Martin Luther King: 41 vacation rentals
  • Historic South Hill: 38 vacation rentals

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

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:

  • Community Park: 112 vacation rentals
  • Lykins Park: 90 vacation rentals
  • Bluegrass Heritage Museum: 111 vacation rentals
  • Clark Regional Medical Center: 115 vacation rentals
  • Daniel Boone National Forest: 404 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 cottages in Winchester?

Yes, of course. VRBO has 4 cottages in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Cabins: 3 rentals available
  • Farmhouses: 2 rentals available

Can I rent golf rental rentals in Winchester?

Absolutely, VRBO has 10 golf rental rentals in Winchester. You have also many other possibilities in Winchester area, including:

  • Beachfront rentals: 4 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with online bookable in Winchester?

Yes, you can select your prefered vacation rental with online bookable among our 13 vacation rentals with online bookable available in Winchester. Please use our search bar to access the selection of vacation rentals available.

    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)

    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)