Leonardtown Vacations from $315

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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.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
Price was $619, price is now $315 per person
$315
per person
Apr 4 - Apr 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
Everything was excellent!

Reviewed on Jan 25, 2026

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Price was $1,347, price is now $377 per person
$377
per person
Apr 4 - Apr 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (2,262 reviews)
Friendly staff. Easy check in. Clean room. New reclining Queen beds. Good maid service. Restaurant food was quiet nice. A very comfortable stay:-)

Reviewed on Jan 30, 2026

West End Washington DC, Tapestry Collection by Hilton

West End Washington DC, Tapestry Collection by Hilton

3 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,158, price is now $790 per person
$790
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,000 reviews)
Clean room, friendly staff

Reviewed on Jan 2, 2026

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Price was $545, price is now $380 per person
$380
per person
Apr 4 - Apr 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,002 reviews)
Room was great. Staff was amd. I'll definitely be back.

Reviewed on Jan 25, 2026

Placemakr Buzzard Point

Placemakr Buzzard Point

2.5 out of 5
Southwest
Save 100% on your flight
Price was $977, price is now $691 per person
$691
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (86 reviews)
Great place and friendly staff

Reviewed on Jan 27, 2026

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Discover the most popular places to visit in Leonardtown

Port of Leonardtown Winery

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
$144 nightly
The price is $159 total per night from Feb 22 to Feb 23
$159 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (163 reviews)
The room was incredibly clean. The women at the front desk made you feel like you were coming to stay at their home. We needed an unpredictable late check out time, and we’re happily accommodated by both the front desk and room attendance staff. I have traveled a lot and I have never had a better ...

Reviewed on Jan 25, 2026

The Inn at Leonardtown, an Ascend Collection Hotel
2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!

Leonardtown MD
10/10 Exceptional! (58 reviews)
The location is amazing!! We had such a fantastic time with gorgeous views. The house is very well equipped and comfortable. We would love to come back!

Reviewed on Sep 28, 2025

Get rates
2 Acre Oasis with Private Beach! Family and dog friendly!
Quality Inn Warsaw near Rappahannock River

Quality Inn Warsaw near Rappahannock River

2.5 out of 5
4522 Richmond Rd Warsaw VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $76 total per night from Feb 22 to Feb 23
$76 total
Feb 22 - Feb 23
Total with taxes and fees
7.4/10 Good! (591 reviews)
As always staff’s terrific

Reviewed on Jan 21, 2026

Quality Inn Warsaw near Rappahannock River
See all 561 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 from $315 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.