Leonardtown Vacation Packages
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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.
Ready to book your vacation to Leonardtown?
Leonardtown Hotel Deals
The Inn at Leonardtown, an Ascend Collection Hotel
41655 Park Avenue Leonardtown MD
Fully refundable
CA $208
CA $231 total
Sep 8 - Sep 9
includes taxes & fees
9.4/10 Exceptional! (183 reviews)
"The staff"
Reviewed on Aug 1, 2026
River Edge Inn
30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
CA $145
CA $175 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very good! (498 reviews)
"Everything perfect. Spectacular location. Great pool! Food choices nearby. Clean room. Comfortable! Ps. Piano at checkin is in tune!"
Reviewed on Aug 13, 2026
avid hotel California - Lexington Park by IHG
23274 Three Notch Road California MD
Fully refundable
CA $129
CA $144 total
Sep 3 - Sep 4
includes taxes & fees
9.4/10 Exceptional! (178 reviews)
"At first Glance, the place was so clean and well lite in and outside. The staff were extremely kind and helpful. Breakfast was included and nice."
Reviewed on Aug 11, 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.
Stay near popular Leonardtown attractions
Breton Bay Golf Course
Enjoy a round of golf in Leonardtown at Breton Bay Golf Course. Take in the festivals and sunsets in the area.
Leonardtown Town Hall
After visiting Leonardtown Town Hall, make a plan to see the other sights and activities in Leonardtown. Take in the festivals and sunsets in the area.
MedStar Saint Mary's Hospital
Though MedStar Saint Mary's Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Leonardtown while you are here.
Miedzinski Park
After visiting Miedzinski Park, make a plan to see the other sights and activities in Leonardtown. Take in the festivals and sunsets in the area.
College of Southern Maryland - Leonardtown Campus
Explore the campus of College of Southern Maryland - Leonardtown Campus during your stay in Leonardtown. Take in the festivals and sunsets in the area.
Leonardtown Library
Leonardtown Library is just one of the places to see in Leonardtown, so why not enjoy the other things to explore during your travels? Take in the festivals and sunsets in the area.
Abell's Wharf
Explore the great outdoors at Abell's Wharf, a lovely green space in Leonardtown. Take in the festivals and sunsets in the area.
Leonard's Grant Recreation Area
After visiting Leonard's Grant Recreation Area, make a plan to see the other sights and activities in Leonardtown. Take in the festivals and sunsets in the area.
Frequently asked questions
How much does a Leonardtown vacation package cost?
You'll find cheap prices on Expedia for your Leonardtown break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Leonardtown costs.
What are the cheapest months to go to Leonardtown?
If you're looking to snag a cheap Leonardtown vacation package, consider planning a trip in January, March and September. You'll typically find lower prices on airfares and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for Leonardtown?
You can visit all the main sights in Leonardtown in a few days, including the must-see New Towne Neck State Park. If you're after a longer Leonardtown vacation, check out what sort of day tours and activities are available close by.
How to find the best Leonardtown package deals?
Begin your search for a Leonardtown package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Leonardtown package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Leonardtown adventure underway.
Is it cheaper to book a Leonardtown vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Leonardtown vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Leonardtown?
If you're considering a spontaneous Leonardtown vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Leonardtown?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Leonardtown.
- Set your budget: Consider expenses such as flights, food and transportation when working out how much to save for your trip to Leonardtown. Then, choose a hotel that suits your budget, whether that's an affordable option or a deluxe retreat.
- Decide your trip length: Think about how long you want to spend discovering Leonardtown. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, book the ideal Leonardtown vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
