Leonardtown Holidays
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Top hotels in Leonardtown
The Inn at Leonardtown, an Ascend Collection Hotel
41655 Park Avenue Leonardtown MD
Fully refundable
S$214
27 Sept - 28 Sept
includes taxes & fees
River Edge Inn
30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
S$131
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very good! (523 reviews)
"The stay started with the amazing staff at the motel and they were very helpful and friendly. It was nice to park right at your door. It had a nice pool with the hotel. The beach is a stones throw away."
Reviewed on 4 Sept, 2026
avid hotel California - Lexington Park by IHG
23274 Three Notch Road California MD
Fully refundable
S$136
9 Sept - 10 Sept
includes taxes & fees
9.4/10 Exceptional! (193 reviews)
"We will definitely stay here again next time we are in the area. New hotel, great staff, great coffee that is freshly ground with each cup. Nice area, safe, plenty of shopping and restaurants nearby."
Reviewed on 5 Sept, 2026
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.
Stay near popular Leonardtown attractions
Leonardtown Town Hall
This historic building serves as the heart of Leonardtown's civic operations and community gatherings. Combine your visit with a stroll through the charming city centre area to experience local culture.
Breton Bay Golf Course
This traditional championship golf course winds through scenic Breton Bay with manicured Bermuda fairways and bent grass greens. Enjoy a round followed by dining at the clubhouse overlooking the picturesque landscape.
Abell's Wharf
Explore the great outdoors at Abell's Wharf, a lovely green space in Leonardtown. Take in the festivals and sunsets in the area.
College of Southern Maryland - Leonardtown Campus
Enjoy the student vibe at College of Southern Maryland - Leonardtown Campus as part of your travels around Leonardtown. Take in the festivals and sunsets in the area.
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.
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.
Indian Village Archeological Park
This archaeological park preserves the heritage of indigenous peoples who once thrived in Maryland. Explore interpretive trails that reveal ancient lifeways amid the tranquil natural landscape.
MedStar Saint Mary's Hospital
If MedStar Saint Mary's Hospital is what brings you to town, hopefully you'll have a chance to explore more of Leonardtown.
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?
- Pick your travel dates: What you'd like to do in Leonardtown and your preferred season will help you decide when to travel.
- 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.
- 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.
- 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
