Leonardtown Vacations from $249

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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.
Studio 6 Springfield, Va – Washington Dc Southwest

Studio 6 Springfield, Va – Washington Dc Southwest

2 out of 5
Price was $313, price is now $249 per person
$249
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
7.8/10 Good! (135 reviews)
Kitchen was a plus, lack of pots pans dishes and utensils were a minus.

Reviewed on Aug 11, 2025

Staybridge Suites Tysons - McLean by IHG

Staybridge Suites Tysons - McLean by IHG

3 out of 5
Save 100% on your flight
Price was $972, price is now $679 per person
$679
per person
Oct 26 - Oct 31
found 8 hours ago
Roundtrip flight included
Dallas (DAL) to Washington (DCA)
9.2/10 Wonderful! (1,002 reviews)
Need to weed the front planters and pick up the trash. Not a very good first impression. Ms. Angel was nice and professional. Please upgrade the property. The life guard was nice.

Reviewed on Jul 30, 2025

Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
Save 100% on your flight
Price was $411, price is now $315 per person
$315
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,000 reviews)
it had a nice clean gym

Reviewed on Aug 17, 2025

Landing Washington DC near Washington Navy Yard

Landing Washington DC near Washington Navy Yard

2 out of 5
Southeast
Save 100% on your flight
Price was $670, price is now $528 per person
$528
per person
Sep 19 - Sep 22
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
No reviews
Hilton Garden Inn Reagan National Airport

Hilton Garden Inn Reagan National Airport

3.5 out of 5
Crystal City
Price was $404, price is now $332 per person
$332
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,694 reviews)
The people at the front desk were not very personable but the hotel was really nice and clean.

Reviewed on Aug 19, 2025

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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, Ascend Hotel Collection

The Inn at Leonardtown, Ascend Hotel Collection

2.5 out of 5
41655 Park Avenue, Leonardtown, MD
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $143 total per night from Sep 14 to Sep 15
$143 total
Sep 14 - Sep 15
Total includes taxes and fees
9/10 Wonderful! (144 reviews)
"Staff was very friendly, room was clean."

Reviewed on Aug 8, 2025

The Inn at Leonardtown, Ascend Hotel Collection
River Edge Inn

River Edge Inn

2.5 out of 5
30 Colonial Ave, Colonial Beach, VA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from Aug 20 to Aug 21
$143 total
Aug 20 - Aug 21
Total includes taxes and fees
8.2/10 Very Good! (348 reviews)
"Was a great stay"

Reviewed on Aug 15, 2025

River Edge Inn
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $174 total per night from Sep 1 to Sep 2
$174 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (869 reviews)
"Grreat spot!"

Reviewed on Aug 17, 2025

Solomons Inn Resort & Marina
See all 541 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.

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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 from $249 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.