Leonardtown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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.

Ready to book your vacation to Leonardtown?

 

Choose your dates

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
The price is CA $197 per night from Dec 6 to Dec 7
CA $197
CA $218 total
Dec 6 - Dec 7
includes taxes & fees
9.4/10 Exceptional! (193 reviews)
"I like how tucked back and clean it is, I also enjoyed the cat cafe that was a block away!"

Reviewed on Nov 10, 2026

The Inn at Leonardtown, an Ascend Collection Hotel
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd California MD
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Nov 13 to Nov 14
CA $127
CA $141 total
Nov 13 - Nov 14
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"very clean comfortable place to stay"

Reviewed on Nov 9, 2026

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

3 out of 5
23274 Three Notch Road California MD
Fully refundable
The price is CA $125 per night from Dec 7 to Dec 8
CA $125
CA $139 total
Dec 7 - Dec 8
includes taxes & fees
avid hotel California - Lexington Park by IHG
See all 570 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

Stay near popular Leonardtown attractions

Port of Leonardtown Winery

8.8/10 (13 reviews)
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.
See properties

Frequently asked questions

How much does a Leonardtown vacation package cost?
You'll find cheap prices on Expedia for your Leonardtown break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Leonardtown costs.
What are the cheapest months to go to Leonardtown?
If you're looking to snag a cheap Leonardtown vacation package, consider planning a trip in January, March and September. You'll typically find lower prices on airfares and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for Leonardtown?
You can visit all the main sights in Leonardtown in a few days, including the must-see New Towne Neck State Park. If you're after a longer Leonardtown vacation, check out what sort of day tours and activities are available close by.
How to find the best Leonardtown package deals?
Begin your search for a Leonardtown package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Leonardtown package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Leonardtown adventure underway.
Is it cheaper to book a Leonardtown vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Leonardtown vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Leonardtown?
If you're considering a spontaneous Leonardtown vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Leonardtown?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Leonardtown.
  2. Set your budget: Consider expenses such as flights, food and transportation when working out how much to save for your trip to Leonardtown. Then, choose a hotel that suits your budget, whether that's an affordable option or a deluxe retreat.
  3. Decide your trip length: Think about how long you want to spend discovering Leonardtown. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, book the ideal Leonardtown vacation package for you.

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