Port of Leonardtown Winery Beach House Rentals & Places to Stay

Find the best beach rentals in Port of Leonardtown Winery - We found 72 exact matches

About Port of Leonardtown Winery Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Port of Leonardtown Winery? PickleTrip™ features more than 72 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Port of Leonardtown Winery. Several of these vacation rentals in Port of Leonardtown Winery are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. PickleTrip™’s rental listings come in all shapes and sizes for large groups, friends, or couples, or wedding retreats in Port of Leonardtown Winery.

PickleTrip™ Offers 72 holiday homes and places to stay in Port of Leonardtown Winery. The site provides unique Airbnb, VRBO, PickleTrip-style accommodations to fit your trip or get away with your friends and family.

PickleTrip™ beachfront rentals give you the best travel experience that makes it easy to find and book the best place to stay at the best destinations.

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Frequently Asked Questions About Port of Leonardtown Winery Beach 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 Beach Home Rentals in Port of Leonardtown Winery:

The average cost for a beach rental in Port of Leonardtown Winery is $362 per night. PickleTrip has a wide assortment of great beachfront homes near Port of Leonardtown Winery that would suit your needs.
Yes, we have 72 beach rentals with pools available in Port of Leonardtown Winery. Check our search bar to find a selection of vacation rentals available near Port of Leonardtown Winery.
Yes, here are the top beach rentals in Port of Leonardtown Winery that allow you to bring your pet:

See all pet-friendly beach rentals in Port of Leonardtown Winery on PickleTrip

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Port of Leonardtown Winery to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 72 properties with private swimming pools or private homes with indoor pools in the Port of Leonardtown Winery area.
About 72 properties in Port of Leonardtown Winery boast of having access to hot tubs.