
Leonardtown Vacations from $311
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Your Leonardtown Vacation
The rich history and coastal scenery are just the start of the things Leonardtown has to offer. Discover the best parts of this captivating city your way with a customized Leonardtown vacation package. A trip to Leonardtown is a terrific opportunity to see the sights. Be sure to look around big-name attractions such as St. Marys River State Park, Port of Leonardtown Winery and New Towne Neck State Park. Whoever you're traveling with and whatever your bank balance, your ultimate Leonardtown vacation is just a few clicks away with Expedia.
The Latest Leonardtown vacation packages

Hotel Arboretum
Reviewed on Jan 23, 2026


Placemakr Buzzard Point
Reviewed on Jan 23, 2026

Kimpton George Hotel by IHG
Reviewed on Jan 5, 2026

Riggs Washington DC
Reviewed on Jan 21, 2026
Discover the most popular places to visit in Leonardtown
Port of Leonardtown Winery
You can enjoy a tasting or tour at Port of Leonardtown Winery during your travels to Leonardtown. Amble around this family-friendly area's riverfront or attend a sporting event.
Leonardtown Hotel Deals

The Inn at Leonardtown, an Ascend Collection Hotel
Everyone is so nice and helpful. Rooms were clean. We will be staying there again when we go visit our son.
Reviewed on Jan 9, 2026

2 Acre Oasis with Private Beach! Family and dog friendly!
The location is amazing!! We had such a fantastic time with gorgeous views. The house is very well equipped and comfortable. We would love to come back!
Reviewed on Sep 28, 2025

Quality Inn Warsaw near Rappahannock River
As always staff’s terrific
Reviewed on Jan 21, 2026
Find the Best Leonardtown Vacation Packages
Leonardtown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,600 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | St. Marys River State Park, Port of Leonardtown Winery and Jefferson Patterson Park and Museum |



















