Leonardtown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Pla Jira
Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.

Top Leonardtown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (2,003 reviews)
Staff was friendly and helpful. Rooms were clean and very nice. Area was quiet and felt safe. We rode scooters to all the monuments and it was so fun. Lots of great places to eat in the area. Would definitely stay here again.

Reviewed on May 27, 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
Save 100% on your flight
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,326 reviews)
Not only is the location outstanding, but the staff were the most capable and welcoming i encountered in the DC area. It is an easy walk to some very good bakeries and restsurants as well. Close to the Potomac and to Georgetown shopping.

Reviewed on May 27, 2024

Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.6/10 Excellent! (1,512 reviews)
Staff is friendly and helpful

Reviewed on May 26, 2024

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,231 reviews)
The staff was pleasant and professional. The property was walking distance to the National Gallery of Art (our primary destination), excellent restaurants and the Metro. Our room had no view, the bathroom was tiny (hard to exit) and our shower was missing half the sliding door. By design? If so, never seen that before. Excellent in- room coffee and the hotel cafe food was also excellent.

Reviewed on May 25, 2024

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9/10 Wonderful! (1,008 reviews)
The hotel is located at a prefect area and is close to all the landmarks. However the property is old and the room is dusty and both the telephones are not working and full of dust. Gym is small and the facility is old. Coffee machine is not working. Though there is complimentary coffee and tea in lobby it seems the staff does not really check whether it’s finished or not. No late check out available. Highly recommend elsewhere that is cost effective.

Reviewed on May 20, 2024

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
The price is CA $166 per night from Jun. 9 to Jun. 10
CA $166
CA $185 total
includes taxes & fees
Jun 9 - Jun 10
9/10 Wonderful! (94 reviews)
"Very clean facility with a friendly staff."

Reviewed on May 20, 2024

The Inn at Leonardtown, Ascend Hotel Collection
Gorgeous Sunsets & Waves Heard From Bed. Why Wait?
Gorgeous Sunsets & Waves Heard From Bed. Why Wait?
Leonardtown
The price is CA $437 per night from May 31 to Jun. 1
CA $437
CA $762 total
includes taxes & fees
May 31 - Jun 1
8.6/10 Excellent! (3 reviews)
Not what we expected
"The curb appeal and overall condition of the property is not what we expected. There was a large construction crane and debris in the yard and the landscaping was not maintained. The bed sheets were not fitting the bed and the beds were not comfortable. The back yard had new grass growing with a ..."

Reviewed on Apr. 20, 2024

Gorgeous Sunsets & Waves Heard From Bed. Why Wait?
River Edge Inn
River Edge Inn
2.5 out of 5
30 Colonial Ave, Colonial Beach, VA
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from May 28 to May 29
CA $137
CA $156 total
includes taxes & fees
May 28 - May 29
8.4/10 Very Good! (165 reviews)
"The hotel staff was great, but we booked that hotel because of the pool and it was closed I was not told until check in"

Reviewed on May 26, 2024

River Edge Inn
See all 503 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Leonardtown vacation package cost?
Discover the best of Leonardtown from as little as CA $987. Choose from a great selection of flights, rental cars and hotels to suit your budget. You can score even better deals when you add a few tours or experiences to your package.
How do I get a cheap travel package to Leonardtown?
Search for flights that suit your schedule, add a hotel to your booking and watch how much you save with a Leonardtown vacation package. It’s that easy! From hotels and flights to rental cars and activities, Expedia makes traveling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 hotel options all over the world to choose from, you’ll never be short of choice.
Where should I stay in Leonardtown?
If you plan to check out Port of Leonardtown Winery, skip commuting and lock in a hotel close by. It’s one of the best attractions in the area.
What are the top hotels in Leonardtown?
Whether you plan to stay for one night or longer in Leonardtown, you’ll get a good night’s sleep at The Inn at Leonardtown, Ascend Hotel Collection. This option is a favorite with lots of travelers.
How far in advance should I book my Leonardtown vacation?
The earlier, the better. Airlines usually release flight tickets up to a year ahead of departure, and this is a great opportunity to land some of the cheapest prices. Just been told you should take all your vacation days next month? Don’t fret. Expedia are never short on fantastic bargains to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Leonardtown travel package include?
That depends on what kind of trip you have in the works. Leonardtown travel deals can include car rentals, flights and hotels. You can mix and match to create the bundle that suits your needs. You can also add on experiences and activities after you’ve booked to score even bigger discounts.
What should I know before booking a Leonardtown travel package?
A travel package can be customized for your circumstances and is an easy way to stretch your hard-earned dollars. How much you include is up to you. Hotels, rental cars and flights — come up with a combination that suits your plans.
Can I choose my airline with a Leonardtown Expedia vacation package?
With a vacation package, you’re in charge. Whether you want to fly to Leonardtown in business or coach, simply choose from the available airline options. Expedia has access to more than 550 partner airlines all over the world.
If I'm not able to travel, can I cancel my Leonardtown vacation package?
It’s impossible to predict what tomorrow might bring, so it’s comforting to know that you can cancel or change your Leonardtown vacation package. If you made your booking in the last 24 hours, you may be eligible for a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Leonardtown

Image for Port of Leonardtown Winery

Port of Leonardtown Winery

4/5(1 review)

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
Image for New Towne Neck State Park

New Towne Neck State Park

Explore the great outdoors at New Towne Neck State Park, a lovely green space in Leonardtown. Take in the festivals and sunsets in the area.

New Towne Neck State Park

Other vacations you might like

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