Leonardtown Vacations

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Find the Best Leonardtown Vacation Packages

Leonardtown Hotel Deals

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

41655 Park Avenue Leonardtown MD
Fully refundable
NT$4,811
NT$5,340 total
Sep 27 - Sep 28
includes taxes & 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 2026/8/24

The Inn at Leonardtown, an Ascend Collection Hotel
River Edge Inn

River Edge Inn

30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
NT$2,783
NT$3,414 total
Sep 20 - Sep 21
includes taxes & fees
River Edge Inn
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

23274 Three Notch Road California MD
Fully refundable
NT$2,941
NT$3,264 total
Sep 8 - Sep 9
includes taxes & 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 2026/8/29

avid hotel California - Lexington Park by IHG
See all 579 properties in Leonardtown
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

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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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?
January, March and September are great times to look for cheap Leonardtown vacation packages. Opting to travel in quieter months means you'll typically find better prices on hotels and flights.
How many days is enough for Leonardtown?
Generally, a handful of days is enough to explore the main sights during your Leonardtown vacation. But if you want to have time to unwind or go on day tours, think about extending your trip.
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.
How to plan a trip to Leonardtown?
  1. Pick your travel dates: What you'd like to do in Leonardtown and your preferred season will help you decide when to travel.
  2. Set your budget: Factor in expenses such as flights, food and transportation when working out how much to put aside for your trip to Leonardtown. Then, choose a hotel that matches your budget, whether that's an affordable stay or a more luxurious retreat.
  3. Decide how long to go away for: Now that you're up to speed on Leonardtown, you can figure out the ideal length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Leonardtown vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.