Leonardtown Vacation Packages

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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.

Top Leonardtown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
per person
Mar. 20 - Mar. 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (1,002 reviews)
Nice property. Offers free shuttle but expects you to pay a "tip" to the driver.

Reviewed on Jan. 22, 2025

Hotel Heron Old Town Alexandria

Hotel Heron Old Town Alexandria

4 out of 5
Old Town Alexandria
per person
Mar. 13 - Mar. 16
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9.6/10 Exceptional! (163 reviews)
Everyone was very kind and helpful

Reviewed on Feb. 6, 2025

The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
per person
Apr. 22 - Apr. 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (1,561 reviews)
Great location. Easily walkable to G-town areas as well the university. Nice hotel.

Reviewed on Jan. 29, 2025

The Hay-Adams

The Hay-Adams

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Apr. 14 - Apr. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (DCA)
9.6/10 Exceptional! (865 reviews)
This is a beautiful and historic hotel just a stones throw from the White House. We also loved the downstairs bar which is warm and cozy and a great vibe. Staff is lovely and the room was classic beauty from a bygone era in the best possible way.

Reviewed on Jan. 9, 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
Apr. 22 - Apr. 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (DCA)
9.2/10 Wonderful! (89 reviews)
Relaxing time and staff was super friendly

Reviewed on Feb. 5, 2025

Ready to book your vacation to Leonardtown?

 

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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 $158 per night from Mar. 2 to Mar. 3
CA $158
CA $176 total
includes taxes & fees
Mar 2 - Mar 3
9/10 Wonderful! (125 reviews)
"Nice small town inn with a couple of excellent dining options nearby. Check in was easy and very friendly. Room was clean, modern, with newer tv and heating units. Nice black out blinds instead of curtains."

Reviewed on Jan. 26, 2025

The Inn at Leonardtown, Ascend Hotel Collection
Springhill Suites by Marriott Prince Frederick
Springhill Suites by Marriott Prince Frederick
3 out of 5
75 Sherry Lane, Prince Frederick, MD
The price is CA $176 per night from Feb. 16 to Feb. 17
CA $176
CA $196 total
includes taxes & fees
Feb 16 - Feb 17
8.4/10 Very Good! (843 reviews)
"Check in was so smooth and quick! Love this place when in town for family events."

Reviewed on Feb. 1, 2025

Springhill Suites by Marriott Prince Frederick
Red Roof Inn Dahlgren - Naval Base
Red Roof Inn Dahlgren - Naval Base
2 out of 5
4661 James Madison Pkwy, King George, VA
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Mar. 3 to Mar. 4
CA $99
CA $109 total
includes taxes & fees
Mar 3 - Mar 4
7.6/10 Good! (438 reviews)
"Convenient"

Reviewed on Jan. 3, 2025

Red Roof Inn Dahlgren - Naval Base
See all 518 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?
You can grab a vacation package to this top destination from CA $752 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.

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