Leonardtown Vacations from $195
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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
Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row
Northwest
Save 100% on your flight
Price was $278, price is now $195 per person
$195
per person
Feb 13 - Feb 15
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,915 reviews)
Restaurant was closed the night of our stay which was disappointing. I also had to pay $70 for “valet” which was just us parking our car in the front and it was never moved so we paid $70 just to have our car sit on the property.
Reviewed on Jan 5, 2026
SIXTY DC
Downtown Washington D.C.
Save 100% on your flight
Price was $833, price is now $501 per person
$501
per person
Feb 14 - Feb 20
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (76 reviews)
Absolutely LOVED the stay!! Johnny was amazing forgot her name but the head of house keeping was amazing!! Best New Years yet!! Planning on coming back for a staycation with the wife where we can just unplug and relax. Just an overall amazing experience.
Reviewed on Jan 6, 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
Save 100% on your flight
Price was $357, price is now $216 per person
$216
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
Staff is great. We love this hotel because it has plenty of self parking, so not having to wait for the valet to get your car every time saves a ton of time. The hotel is within the Gallaudet campus which is beautiful and feels very safe. The only issue we had were with the room itself. The furniture and fixtures are a bit dated/worn, though the beds are very comfortable. The sink drain was frozen in the bathroom, the toilet flusher was stuck. We managed to get around these things since we were only there one night and it would not deter us from coming again.
Reviewed on Dec 11, 2025
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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
41655 Park Avenue Leonardtown MD
Fully refundable
$138 nightly
The price is $154 total per night from Feb 2 to Feb 3
$154 total
Feb 2 - Feb 3
Total with taxes and fees
9.2/10 Wonderful! (157 reviews)
No issues
Reviewed on Jan 4, 2026
2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown MD
10/10 Exceptional! (58 reviews)
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
Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown MD
$538 nightly
The price is $570 total per night from Jan 11 to Jan 12
$570 total
Jan 11 - Jan 12
Total with taxes and fees
9.2/10 Wonderful! (5 reviews)
The home was inviting. Everything was provided. Although it looks small from the road, it is spacious in how it was laid out.
Reviewed on Sep 7, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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 |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
