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.
Hotel Heron Old Town Alexandria

Hotel Heron Old Town Alexandria

4 out of 5
Old Town Alexandria
per person
Mar. 28 - Mar. 30
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.6/10 Exceptional! (130 reviews)
Amazing hotel and location

Reviewed on Jan. 2, 2025

The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Feb. 9 - Feb. 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Washington (DCA)
8.8/10 Excellent! (1,534 reviews)
The room was beautiful, with coffee, little handcrafted chocolate truffle, water, spacious bathroom with great mirrors for putting on makeup, well lit, and with thoughful supplies of slippers and robes. I particularly loved the speakeasy downstairs. I did not get to check out the rooftop patio but I hope to return and do so one day. It is unique and idyllic. I will stay here again!

Reviewed on Jan. 2, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
per person
Feb. 8 - Feb. 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Washington (DCA)
9.4/10 Exceptional! (1,009 reviews)
I love the views. But it has changed since the property was the mandarin oriental. It needs to be renovated and updated.

Reviewed on Jan. 2, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
per person
Feb. 9 - Feb. 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Washington (DCA)
8.4/10 Very Good! (1,001 reviews)
The hotel is very average. For the amount we paid per night I was expecting way more. The hotel is outdated, the rooms and service were average. Not really worth it in my opinion.

Reviewed on Jan. 2, 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
Mar. 20 - Mar. 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
9.4/10 Exceptional! (24 reviews)
Easy to walk to Caps or Wizards game. Wise guys pizza is also walkable. 35$ urban fee at checkout was a surprise.

Reviewed on Jan. 4, 2025

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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 Jan. 19 to Jan. 20
CA $158
CA $176 total
includes taxes & fees
Jan 19 - Jan 20
9/10 Wonderful! (122 reviews)
"I liked the parking proximity and availability."

Reviewed on Dec. 10, 2024

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
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Jan. 8 to Jan. 9
CA $156
CA $173 total
includes taxes & fees
Jan 8 - Jan 9
8.4/10 Very Good! (838 reviews)
"Easy check in. Lots of parking. Able to get a handicap room. Very good breakfast offerings."

Reviewed on Dec. 28, 2024

Springhill Suites by Marriott Prince Frederick
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
2.5 out of 5
22769 Three Notch Rd, California, MD
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Jan. 16 to Jan. 17
CA $134
CA $149 total
includes taxes & fees
Jan 16 - Jan 17
7.6/10 Good! (1,000 reviews)
"the hotel staff was kind and attentive"

Reviewed on Dec. 20, 2024

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
See all 509 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 $780 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.