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
Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum
Northeast
Price was $478, price is now $311 per person
$311
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,178 reviews)
Hotel/room was very clean, and everyone was super nice! The manager Toni runs the place like a well oiled machine!!
Reviewed on Jan 23, 2026
Placemakr Buzzard Point
Southwest
Save 100% on your flight
Price was $544, price is now $378 per person
$378
per person
Feb 25 - Mar 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (86 reviews)
Clean apartment with a very good kitchen and bathroom a little bit to far from Downtown Washington but I do suggest this place…
Reviewed on Jan 23, 2026
Kimpton George Hotel by IHG
Northwest
Save 100% on your flight
Price was $894, price is now $632 per person
$632
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,001 reviews)
Friendly staff, convenient to monuments, parking. Nice furnishings.
Reviewed on Jan 5, 2026
Riggs Washington DC
Downtown Washington D.C.
Save 100% on your flight
Price was $1,022, price is now $743 per person
$743
per person
Mar 31 - Apr 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,438 reviews)
The hotel was stunning. It is located in the heart of DC. It was within walking distance of all the museums/monuments, as well as some stunning restaurants. It felt safe and clean and the staff were very kind and accommodating as well as knowledgeable on the city and the hotel. Wouldn't hesitate to stay here again when we come to DC next time. Just book it already
Reviewed on Jan 21, 2026
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See all available trips from Columbus to Leonardtown
View all tripsDiscover the most popular places to visit in Leonardtown
Port of Leonardtown Winery
4.5/5(10 reviews)
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
$144 nightly
The price is $159 total per night from Feb 15 to Feb 16
$159 total
Feb 15 - Feb 16
Total with taxes and fees
9.2/10 Wonderful! (159 reviews)
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!
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
Quality Inn Warsaw near Rappahannock River
4522 Richmond Rd Warsaw VA
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $72 total per night from Feb 22 to Feb 23
$72 total
Feb 22 - Feb 23
Total with taxes and fees
7.4/10 Good! (590 reviews)
As always staff’s terrific
Reviewed on Jan 21, 2026
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.
