36+ Winchester Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Winchester

Discover more than 36 holiday rentals in Winchester. Rent By Owner holiday homes has everything you need to find a place to stay near Winchester, KY.

Whether you are looking for luxury villas in Winchester, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Winchester with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Winchester for families, large parties, or private owner accommodations for long or short trips. Winchester Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Winchester with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Winchester Holiday Rentals

There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Winchester:

There are many holiday rentals available in Winchester; however, here are a few of the most popular holiday homes listed in Winchester on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Winchester to find one that works for you.
Yes, there are 36 self-catering family homes and holiday rentals in Winchester.
There are more than 36 luxury holiday homes in or near Winchester, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: