Leonardtown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Pla Jira

Top hotels in Leonardtown

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 3.319.284 ₫ per night from 13 Jul to 14 Jul
3.319.284 ₫
3.684.405 ₫ total
13 Jul - 14 Jul
includes taxes & fees
9/10 Wonderful! (136 reviews)
"Nice property in a convenient area. Staff was very friendly."

Reviewed on 9 Jun 2025

The Inn at Leonardtown, Ascend Hotel Collection
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 3.264.484 ₫ per night from 6 Jul to 7 Jul
3.264.484 ₫
3.623.577 ₫ total
6 Jul - 7 Jul
includes taxes & fees
7.8/10 Good! (811 reviews)
Fabulous
"Wonderful stay for my friends birthday.Janai at front desk was exceptional in getting birthday care for the room and assuring a waterfront room. Janai and my friend shared the same birthday. Everyone was so nice and accommodating. Will be my new getaway spot."

Reviewed on 24 Jun 2025

Solomons Inn Resort & Marina
My Place Hotel - Dahlgren/King George, VA
My Place Hotel - Dahlgren/King George, VA
2.5 out of 5
4235 Market Center Drive, King George, VA
Fully refundableReserve now, pay when you stay
The price is 1.976.305 ₫ per night from 13 Jul to 14 Jul
1.976.305 ₫
2.179.865 ₫ total
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (511 reviews)
"I have stayed there several times and has always been great. Seems as though the AC wasn't working well in room 206 however. I woke up multiple times during the night because it got hot."

Reviewed on 26 Jun 2025

My Place Hotel - Dahlgren/King George, VA
See all 531 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.

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.

Popular places to visit

Port of Leonardtown Winery

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.

Port of Leonardtown Winery