Winchester Vacation Rentals, Lexington: homes, house rentals & more

Discover a selection of vacation rentals in Winchester that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the amenities you need and want for your stay, which might include WiFi and a pool. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

Find the best place to stay - Winchester

The Kentucky Dream Estate

Sleeps 50 · 14 bedrooms · 8 bathrooms

Beautifully nestled back in nature close to the Red River Gorger area!

Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge, Kentucky!

Sleeps 4 · 1 bedroom · 1 bathroom

Find spaces that suit your style

Top rated rentals - Winchester

Wonderful Experience!

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

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.

Frequently asked questions

How much does it cost to rent a vacation rental in Winchester?

A number of things influence what you'll pay for a vacation rental in Winchester, like the season, length of stay and type of property. Still, all of our vacation homes have one thing in common — incredible value. Simply enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Winchester?

The average price for a vacation rental near the beach in Winchester will depend on when you're going and the style and size of property you're searching for. You can quickly and easily find prices on Vrbo by entering your destination and preferred travel dates. Then use the handy filters to select the number of bedrooms and amenities that you need, like air conditioning, WiFi and a hot tub.

What are the top attractions for families in Winchester?

You'll find loads of fabulous things to do and see with the family in Winchester, such as:

Bluegrass Heritage Museum
Lykins Park
Southwind Golf Course

How old do you have to be to rent a vacation rental in Winchester?

The minimum required age is usually 16, 18 or 21. It can vary from property to property on Vrbo, so look at the rules of your preferred Winchester vacation rental before booking your stay.

How long can I rent a vacation rental in Winchester for?

The amount of time you can rent a Winchester vacation home for is down to each property. Simply tap in your travel dates to find available options offering longer term stays. They come with all you need to make your extended getaway more comfortable like kitchens and laundries. Some vacation homes might also offer weekly or monthly discounts, so you can stay longer for less money.