Port of Leonardtown Winery Cottage Rentals & Holiday Homes

Find the best cottages in Port of Leonardtown Winery - We found 29 exact matches

About Port of Leonardtown Winery Cottage Rentals on Rent By Owner

Searching for cottages to rent near Port of Leonardtown Winery? Rent By Owner features more than 29 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Port of Leonardtown Winery have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. RBO’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Port of Leonardtown Winery.

Are you planning to travel to the lakeside, beach, or mountain area? RBO’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Rent By Owner boasts of 29 holiday cottages and places to stay in Port of Leonardtown Winery. The site provides unique Airbnb, VRBO, RBO-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

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Frequently Asked Questions About Port of Leonardtown Winery Rental Cottages

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 Cottage Rentals in Port of Leonardtown Winery:

The average cost for a cottage rental in Port of Leonardtown Winery is $255 per night. RBO has a wide list of great cottages near Port of Leonardtown Winery that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Port of Leonardtown Winery that allow you to bring your pet:

See all pet-friendly vacation rentals in Port of Leonardtown Winery on Rent By Owner

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Port of Leonardtown Winery to find one that works for you.
As of 2025, the data from Rent By Owner shows that there are Over 29 private swimming pools or cottages with indoor pools in the Port of Leonardtown Winery area along with other great amenities.