217+ Port of Leonardtown Winery Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Port of Leonardtown Winery

Discover more than 217 holiday rentals in Port of Leonardtown Winery. Rent By Owner holiday homes has everything you need to find a place to stay near Port of Leonardtown Winery, MD.

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

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Frequently Asked Questions About Port of Leonardtown Winery Holiday Rentals

There are a lot of options in Port of Leonardtown Winery. If you plan on staying in the Port of Leonardtown Winery 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 Port of Leonardtown Winery:

There are many holiday rentals available in Port of Leonardtown Winery; however, here are a few of the most popular holiday homes listed in Port of Leonardtown Winery 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 Port of Leonardtown Winery to find one that works for you.
Yes, there are 217 self-catering family homes and holiday rentals in Port of Leonardtown Winery.
There are more than 217 luxury holiday homes in or near Port of Leonardtown Winery, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: