Leonardtown Vacations
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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.
Stay near popular Leonardtown attractions
Breton Bay Golf Course
This traditional championship golf course winds through scenic Breton Bay with manicured Bermuda fairways and bent grass greens. Enjoy a round followed by dining at the clubhouse overlooking the picturesque landscape.
Leonardtown Town Hall
This historic building serves as the heart of Leonardtown's civic operations and community gatherings. Combine your visit with a stroll through the charming downtown area to experience local culture.
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.
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.
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.
Leonard's Grant Recreation Area
This community hub offers scenic trails, sports courts, and a welcoming clubhouse in Leonardtown. Attend seasonal events or enjoy a peaceful afternoon picnic in the well-maintained green spaces.
Port of Leonardtown Winery
8.8/10 (13 reviews)
This cooperative winery unites 12 local vineyards to produce award-winning wines from Maryland-grown grapes. Enjoy tastings in a relaxed setting or bring a picnic to savor on the covered patio.
Leonardtown Park
This waterfront park on Breton Bay blends history with modern recreation in a serene setting. Enjoy kayaking, sunset strolls along the boardwalk, or attend seasonal events like the Water's Edge Music Series.
Leonardtown Hotel Deals
The Inn at Leonardtown, an Ascend Collection Hotel
41655 Park Avenue Leonardtown MD
Fully refundable
$152 nightly
$169 total
Sep 21 - Sep 22
Total with taxes and fees
9.4/10 Exceptional! (186 reviews)
"The room was pretty clean. The toilet was not secure on the tile floor so when you sat and got up it moved. The tub could've been cleaned better and there was an unpleasant odor in the hallway and stairway. Room walls are very thin so you can hear your neighbor talking through wall."
Reviewed on Aug 24, 2026
River Edge Inn
30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
$113 nightly
$124 total
Aug 31 - Sep 1
Total with taxes and fees
avid hotel California - Lexington Park by IHG
23274 Three Notch Road California MD
Fully refundable
$93 nightly
$103 total
Sep 8 - Sep 9
Total with taxes and fees
9.4/10 Exceptional! (189 reviews)
"Shiny new property. Conveniently located. Ample parking. Shopping and restaurants galore but you must drive. No matter. A great place to stay."
Reviewed on Aug 29, 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
How much does a Leonardtown vacation package cost?
You can grab a vacation package to this top destination on Expedia. But how much your vacation to Leonardtown costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Leonardtown?
You can typically find reduced prices and greater availability in January, February and August. Explore our cheap Leonardtown vacation packages and you could score some great off-season discounts.
How many days is enough for Leonardtown?
With a well-organized itinerary, you can easily hit the top Leonardtown sights in a handful of days. But if you prefer to venture off the beaten track or take day trips, think about booking your Leonardtown vacation for longer.
How to find the best Leonardtown package deals?
Finding a cheap Leonardtown package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Leonardtown package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Leonardtown vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and stays separately. Better still, you can personalize your Leonardtown getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Leonardtown?
Land fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Leonardtown trip.
Does Expedia offer Book Now, Pay Later Leonardtown vacation packages?
Your Leonardtown break is meant to be an escape from your busy life, not a source of money-related stress. So to give you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.