Leonardtown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
per person
Jun. 4 - Jun. 8
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.2/10 Very Good! (1,006 reviews)
We were visiting our niece at Gallaudet University. Everything is walkable. Parking is available nearby for a fee. Metro is nearby as well. Overall, we had a pleasant trip.

Reviewed on Mar. 9, 2025

The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Jun. 4 - Jun. 8
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (1,583 reviews)
Hotel is cosmetically attractive but mechanically wanting. Shower is gorgeous if only there was water pressure. Sinks are beautiful but faucets are installed the wrong way. No hooks for robes or used towels. Could not cool the room without opening a window.

Reviewed on Mar. 10, 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Save 100% on your flight
per person
Jun. 4 - Jun. 8
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (1,416 reviews)
The Lyle doesn’t disappoint-classy, nicely updated and comfortable. Only comment is restaurant was understaffed one morning for breakfast-

Reviewed on Mar. 9, 2025

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Jun. 4 - Jun. 8
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (2,326 reviews)
Close to the German Embassy.

Reviewed on Mar. 10, 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Save 100% on your flight
per person
Jun. 4 - Jun. 8
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (179 reviews)
Very nice hotel that had large rooms and was conveniently located near attractions. Will stay again

Reviewed on Mar. 11, 2025

Ready to book your vacation to Leonardtown?

 

Choose your dates

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 $178 per night from Apr. 6 to Apr. 7
CA $178
CA $198 total
includes taxes & fees
Apr 6 - Apr 7
9/10 Wonderful! (128 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
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 $137 per night from Mar. 23 to Mar. 24
CA $137
CA $153 total
includes taxes & fees
Mar 23 - Mar 24
7.6/10 Good! (1,002 reviews)
"Consistent 3 years in a row. Will be back for my son’s swim champs in 6 months"

Reviewed on Mar. 9, 2025

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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
The price is CA $188 per night from Mar. 20 to Mar. 21
CA $188
CA $208 total
includes taxes & fees
Mar 20 - Mar 21
7.8/10 Good! (758 reviews)
"Staff was great. Good breakfast. Easy parking and very clean. Pleasantly surprised for not being associated with a big hotel chain."

Reviewed on Mar. 9, 2025

Solomons Inn Resort & Marina
See all 523 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 $852 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.