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.

Discover 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.

Port of Leonardtown Winery

Leonardtown Hotel Deals

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

2.5 out of 5
41655 Park Avenue Leonardtown MD
Fully refundable
$142 nightly
The price is $157 total per night from Jun 14 to Jun 15
$157 total
Jun 14 - Jun 15
Total with taxes and fees
The Inn at Leonardtown, an Ascend Collection Hotel
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

3 out of 5
23274 Three Notch Road California MD
Fully refundable
$106 nightly
The price is $118 total per night from May 25 to May 26
$118 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (88 reviews)
"I like that the property was practically new, decor was great, staff was attentive and helpful, area was close to restaurant and stores. I was very surprise of how small the rooms were, not dresser, no closet, but the room decor was wonderful, bathroom was large. Great place for a short visit to ..."

Reviewed on May 18, 2026

avid hotel California - Lexington Park by IHG
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd California MD
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $101 total per night from May 24 to May 25
$101 total
May 24 - May 25
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
"It was a quick stay as I was only in town for one night. I was impressed by the friendliness of the staff. Everyone with whom I came into contact was smiling, helpful, warm, and welcoming. I particularly would like to mention Allen who was attending to the breakfast buffet. He was thorough and so ..."

Reviewed on May 16, 2026

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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.

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.