Winchester vacation rentals
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Find the best place to stay - Winchester
The Kentucky Dream Estate
Top rated rentals - Winchester
Photo gallery for Farmhouse living within sight of Lexington - Horse Paddock available
Hidden Gem
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- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
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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. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.
Activities and attractions in and around Winchester
Are you hoping to discover attractions to visit during your stay? Venture out of your vacation home and experience everything that makes Winchester a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:
- Claiborne Farm (14.5 mi / 23.4 km)
- Talon Winery (15.5 mi / 24.9 km)
- Kearney Hills Golf Links (21.3 mi / 34.2 km)
- Southwind Golf Course (2.2 mi / 3.5 km)
- Connemara Golf Course (20.9 mi / 33.7 km)
- Cassell Creek Golf Course (4.1 mi / 6.6 km)
Exploring the natural features in Winchester
Whether you're an outdoor enthusiast or just want to take in the scenery, Winchester is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:
- Kentucky Horse Park (21.3 mi / 34.3 km)
- Lake Reba (18 mi / 29 km)
- Masterson Station Park (21.7 mi / 34.9 km)
- Community Park (0.9 mi / 1.4 km)
- Raven Run Nature Sanctuary (13.3 mi / 21.3 km)
- Jacobson Park (13.4 mi / 21.5 km)
Traveling to and around Winchester
The nearest airport is in Blue Grass Airport (LEX), located 23 mi (37.1 km) from the city center.