Port of Leonardtown Winery Cottage Rentals & Holiday Homes

Find the best cottages in Port of Leonardtown Winery - We found 30 exact matches

About Port of Leonardtown Winery Cottage Rentals on PickleTrip

Searching for cottages to rent near Port of Leonardtown Winery? PickleTrip™ features more than 30 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. 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. PickleTrip™’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? PickleTrip™’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.

PickleTrip™ boasts of 30 holiday cottages and places to stay in Port of Leonardtown Winery. The site provides unique Airbnb, VRBO, pickleball-ready 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.

Show more
Show less

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 $254 per night. PickleTrip 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 PickleTrip

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 PickleTrip shows that there are Over 30 private swimming pools or cottages with indoor pools in the Port of Leonardtown Winery area along with other great amenities.
About 30 cottages in Port of Leonardtown Winery boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Port of Leonardtown Winery on PickleTrip
Yes, there are luxury cottages in Port of Leonardtown Winery. Find more luxury, lakefront, winter, & last-minute cottage rentals near Port of Leonardtown Winery.