Leonardtown, MD

Travel Guide

A rural landscape with a barn, trees, and a fence under a sunset sky.
A lakeside view with trees, a wooden dock, and a small shed.
A wooden pier extending into calm water with a clear sky and distant land.
A driftwood log on a sandy beach with the ocean in the background.
A snow-covered residential area with houses and a street lamp.
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
$140 nightly
The price is $155 total per night from Dec 6 to Dec 7
$155 total
Dec 6 - Dec 7
Total with taxes and fees
Stay at this hotel in Leonardtown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
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
$92 nightly
The price is $102 total per night from Dec 6 to Dec 7
$102 total
Dec 6 - Dec 7
Total with taxes and fees
Book a stay at this business-friendly hotel in California. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,000 reviews)
"They kicked us out over nothing the room keeper lied on us, the staff even said they would’ve gave my deposit back the room keeper didn’t even speak English and was just lying, would wanna see the camera footage cause that’s my money they playing with"

Reviewed on Nov 2, 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
$93 nightly
The price is $103 total per night from Nov 19 to Nov 20
$103 total
Nov 19 - Nov 20
Total with taxes and fees
Book a stay at this business-friendly hotel in California. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Wildewood Shopping Center ...
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.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict MD
Book a stay at this beach cottage in Benedict. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Main Beach and Long Point are located ...
9/10 Wonderful! (16 reviews)
"It was clean and very family friendly. Sophia was awesome and was easy to communicate with! We had a great fall weekend!"

Reviewed on Oct 18, 2026

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Fall Cove Mornings & Fireside Nights in St Inigoes

Fall Cove Mornings & Fireside Nights in St Inigoes

St Inigoes MD
Stay at this vacation home in Saint Inigoes. Enjoy a garden, laundry facilities, and patios. Popular attractions Historic St. Mary's City and Saint Inigoes State ...
Fall Cove Mornings & Fireside Nights in St Inigoes
Tiny, Funky, and Full of Love - Welcome to the Love Shack

Tiny, Funky, and Full of Love - Welcome to the Love Shack

Piney Point MD
Stay at this apartment in Piney Point. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Piney Point Beach and Piney Point Lighthouse are ...
9.8/10 Exceptional! (42 reviews)
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Reviewed on Nov 1, 2026

Tiny, Funky, and Full of Love - Welcome to the Love Shack
See all 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.

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

Is Leonardtown worth visiting?
Leonardtown is worth visiting for its local dining, offering Italian dishes like pasta and classic North American cuisine. Travelers can also explore standout attractions such as Leonardtown Town Hall and enjoy the outdoors at Leonardtown Park.
When is the best time to visit Leonardtown?
The best time to visit Leonardtown is from May through September, when the climate is most pleasant for exploring. For fewer crowds and better value, the quieter months of November through February are a good option, offering a more relaxed experience with cooler weather.
What is a good itinerary length for Leonardtown?
A good itinerary length for Leonardtown is one to two days to explore highlights like Leonardtown Town Hall, Leonardtown Park, and Abell's Wharf. For a more relaxed trip, consider three to four days, allowing time to enjoy the local Italian, North American, or European dining options and further discover the area.
What are the top things to do in and around Leonardtown?
In Leonardtown, travelers can enjoy natural spaces, local landmarks, and outdoor recreation:

  • Explore Leonardtown Town Hall.
  • Stroll through Leonardtown Park.
  • Visit Abell's Wharf, a natural area.
  • Play a round at Breton Bay Golf Course.
  • Discover New Towne Neck State Park.

How do I plan a trip to Leonardtown?
To plan your trip to Leonardtown, book flights, hotels, and a rental car ahead of time. You can explore attractions such as Leonardtown Town Hall, Leonardtown Park, and Abell's Wharf. For outdoor plans, always consider indoor alternatives to stay flexible with changing weather.
What cuisines can you find in Leonardtown?
In Leonardtown you can find Italian cuisine, offering classics such as pasta, pizza, and risotto, alongside delicious desserts like tiramisu. Travelers can also explore a variety of North American favorites, European dishes, and diverse Asian and Latin American options.
Can I book a refundable hotel in Leonardtown?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Leonardtown by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Leonardtown with Expedia?
Expedia makes it easier to plan your Leonardtown trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Leonardtown?
The best choice depends on your travel style. Hotels in Leonardtown can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Leonardtown trip on Expedia?
Once you've booked your Leonardtown trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Leonardtown trip?
Expedia offers customer support before, during, and after your Leonardtown trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Leonardtown?
If it's your first trip to Leonardtown, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Leonardtown hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Leonardtown hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Leonardtown

The Golden Gate Bridge spanning the San Francisco Bay with a cityscape in the background.

California

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