Leonardtown Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

Stay near popular Leonardtown attractions

Sandyland Beach

This secluded shoreline offers a tranquil escape from Maryland's busier beaches along the Chesapeake Bay. Bring your own supplies and enjoy the unspoiled natural setting perfect for peaceful beachcombing.
See properties

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
$152 nightly
The price is $169 total per night from Jul 26 to Jul 27
$169 total
Jul 26 - Jul 27
Total with taxes and fees
9.4/10 Exceptional! (181 reviews)
"This hotel is very cute, clean and centrally located to the downtown Leonardtown area. Parking was very accessible and easy and I loved that breakfast was included. My only issue was the woman working at the front desk when we checked in. She was grumpy and not very friendly. We arrived at noon so ..."

Reviewed on Jun 23, 2026

The Inn at Leonardtown, an Ascend Collection Hotel
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
$91 nightly
The price is $101 total per night from Jul 8 to Jul 9
$101 total
Jul 8 - Jul 9
Total with taxes and fees
9.4/10 Exceptional! (141 reviews)
"A good over night accommodation. Staff was very helpful and friendly. Plenty of eating places near by. A good place to stay if your touring Southern Maryland."

Reviewed on Jul 1, 2026

avid hotel California - Lexington Park by IHG
River Edge Inn

River Edge Inn

2.5 out of 5
30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $124 total per night from Jul 8 to Jul 9
$124 total
Jul 8 - Jul 9
Total with taxes and fees
8.2/10 Very Good! (461 reviews)
"The bathroom had balls of dark colored hair, the bathroom did not look cleaned. The toilet seat would fall off when you would sit on it. The best part. I found wet bathing suits in the Armour that didn't belong to me."

Reviewed on Jul 4, 2026

River Edge Inn
See all 574 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.

Find the Best Leonardtown Vacation Packages

Leonardtown Essential Information

Language
English
Currency
U.S dollars
Population
3,600
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
St. Marys River State Park, Port of Leonardtown Winery and Jefferson Patterson Park and Museum

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Leonardtown vacation package cost?
You can grab a vacation package to this top destination 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?
You can typically find reduced prices and greater availability in January, February and August. Explore our cheap Leonardtown vacation packages and you could score some great off-season discounts.
How many days is enough for Leonardtown?
With a well-organized itinerary, you can easily hit the top Leonardtown sights in a handful of days. But if you prefer to venture off the beaten track or take day trips, think about booking your Leonardtown vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Leonardtown vacation packages?
Your Leonardtown break is meant to be an escape from your busy life, not a source of money-related stress. So to give you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.