St. Leonard, MD

Travel Guide

A beach at sunset with a wooden fence in the background.
A beach at sunset with waves, birds, and a clear sky.
A beach with waves at sunset.
A sunset over a beach with waves and a distant shoreline.
Historic 1825 Chesapeake Farm Stay

Historic 1825 Chesapeake Farm Stay

2 out of 5
1380 Wagner Street St. Leonard MD
The price is $142 total per night from Sep 24 to Sep 25
$142 total
per night
Sep 24 - Sep 25
Book a stay at this family-friendly B&B in St. Leonard. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vera's White Sands Marina and ...
10/10 Exceptional! (2 reviews)
"I booked a weekend stay here for my wife and I for our 30th anniversary. The house was amazing. There has been a lot of effort put into its decor which adds plenty of character to this historic hosue.Its very warm and welcoming. We were greeted by Holly upon our arrival she made us feel comfortable ..."

Reviewed on Sep 14, 2026

Historic 1825 Chesapeake Farm Stay
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard MD
The price is $262 total per night from Sep 30 to Oct 1
$262 total
per night
Sep 30 - Oct 1
Stay at this vacation home in St. Leonard. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Flag Harbor Marina and Long ...
10/10 Exceptional! (8 reviews)
"we had a slight issue with getting access via the passcode but the owners were very responsive and fixed the problem right away other than that minor inconvenience everything was fine and comfortable."

Reviewed on Aug 23, 2026

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard MD
Book a stay at this family-friendly vacation home in St. Leonard. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jefferson Patterson ...
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Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
See all 491 properties in St. Leonard
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.
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard MD
Stay at this vacation home in St. Leonard. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Flag Harbor Marina and Long ...
10/10 Exceptional! (8 reviews)
"we had a slight issue with getting access via the passcode but the owners were very responsive and fixed the problem right away other than that minor inconvenience everything was fine and comfortable."

Reviewed on Aug 23, 2026

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard MD
Book a stay at this family-friendly vacation home in St. Leonard. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jefferson Patterson ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD
Book a stay at this family-friendly vacation home in Cambridge. Enjoy free WiFi, private pools, and a garden. Popular attractions Christ Rock Park and Spocott ...
9.6/10 Exceptional! (98 reviews)
"Excellent house, 100% recommended. We were a group of 15 people, 5 of them with disabilities, 3 with wheelchairs, still the house was very suitable for everyone."

Reviewed on Sep 15, 2026

Private 2 Acre Waterfront Family Retreat with Pool & Pier
See all properties in St. Leonard
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 St. Leonard attractions

Matoaka Beach

Why not spend a lazy afternoon at Matoaka Beach during your trip to St. Leonard? Amble around the area's parks or visit its shops.
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Frequently asked questions

Is St. Leonard worth visiting?
St. Leonard is worth visiting for its standout attractions and experiences. Travelers can enjoy the scenic Matoaka Beach, perfect for relaxing by the water, and explore the historical Jefferson Patterson Park and Museum, which offers insights into the area's heritage and natural surroundings.
When is the best time to visit St. Leonard?
The best time to visit St. Leonard is from May through September, when the climate is generally most pleasant for travelers. For fewer crowds and better value, the quieter months of November through February are a good bet, offering a cooler climate for your travels.
What is St. Leonard known for?
St. Leonard is known for Matoaka Beach, a popular spot for travelers to enjoy the water. The area also features the Jefferson Patterson Park and Museum, offering cultural and historical experiences, alongside the Flag Harbor Marina, which caters to boating activities.
What is a good itinerary length for St. Leonard?
A good itinerary length for St. Leonard is one to two days to enjoy Matoaka Beach and Jefferson Patterson Park and Museum. For a more relaxed trip, three to four days allows travelers to also explore Flag Harbor Marina and spend more time experiencing the area's natural beauty and history.
What are the top things to do in and around St. Leonard?
St. Leonard offers travelers beautiful natural spaces and coastal spots to explore. You can:

  • Visit Matoaka Beach for a relaxing day by the water
  • Explore Jefferson Patterson Park and Museum, which combines nature with history
  • See Flag Harbor Marina, a local landmark
  • Stroll along Long Beach and enjoy the natural surroundings

How do I plan a trip to St. Leonard?
To plan your trip to St. Leonard, search for flights and hotels on Expedia. Book activities like visiting Matoaka Beach, Jefferson Patterson Park and Museum, and Flag Harbor Marina in advance. Remember to pair your outdoor plans with indoor backups for weather flexibility. Consider booking a rental car to explore the area at your own pace.
Can I book a refundable hotel in St. Leonard?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in St. Leonard 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 St. Leonard with Expedia?
Expedia makes it easier to plan your St. Leonard 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 St. Leonard?
The best choice depends on your travel style. Hotels in St. Leonard 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 St. Leonard trip on Expedia?
Once you've booked your St. Leonard 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 St. Leonard trip?
Expedia offers customer support before, during, and after your St. Leonard 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 St. Leonard?
If it's your first trip to St. Leonard, 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 St. Leonard 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 St. Leonard hotel.

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

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