Leonardtown Holidays

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Your Leonardtown Holiday

There's no better way to embark on an adventure than with one of our holiday packages to Leonardtown. The rich history and coastal scenery are two of the convincing reasons to spend some time in this captivating city. St. Marys River State Park, Port of Leonardtown Winery and New Towne Neck State Park are just some of the sights you'll want to check out during your trip to Leonardtown. Don't delay visiting this city any longer. The ultimate Leonardtown holiday is only a few clicks away with Expedia.

Leonardtown Holiday

Leonardtown Essential Information

Language
English
Currency
U.S dollars
Population
3,600
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
St. Marys River State Park, Jefferson Patterson Park and Museum and Patuxent River Naval Air Museum

Our pick of the best 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 AU$224 per night from 23 Nov to 24 Nov
AU$224
23 Nov - 24 Nov
includes taxes & fees
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 AU$148 per night from 25 Nov to 26 Nov
AU$148
25 Nov - 26 Nov
includes taxes & fees
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
The price is AU$147 per night from 12 Nov to 13 Nov
AU$147
12 Nov - 13 Nov
includes taxes & fees
9.4/10 Exceptional! (237 reviews)
"Place was clean and the staff was very friendly. The rooms were advertised as sound proof, but that was not the case."

Reviewed on 24 Oct 2026

avid hotel California - Lexington Park by IHG
See all 571 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Leonardtown attractions

Port of Leonardtown Winery

8.8/10 (13 reviews)
This cooperative winery unites 12 local vineyards to produce award-winning wines from Maryland-grown grapes. Enjoy tastings in a relaxed setting or bring a picnic to savour on the covered patio.
See properties

Frequently asked questions

How much does a Leonardtown holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday 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 holiday 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 holiday. 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 customise 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 holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging flights and stays separately. Better still, you can personalise 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 holiday 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 holiday 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.