St. Leonard Vacations
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Your St. Leonard Vacation
Prepare to experience St. Leonard your way with a custom St. Leonard vacation package! Discovering the best parts of this lively city is made simpler with a base in a neighborhood such as Solomons Island, which is good for fishing, among plenty of other things. Love to get out and explore? Jefferson Patterson Park and Museum, Battle Creek Cypress Swamp Sanctuary and Perigeaux Vineyards and Winery are three of the top places to visit during a trip to St. Leonard. Your perfect St. Leonard vacation is a few clicks away. Browse flights, accommodations and more on Expedia for a trip that's tailored to suit your travel style.
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.
Jefferson Patterson Park and Museum
You can spend an afternoon exploring the galleries in Jefferson Patterson Park and Museum during your trip to St. Leonard. Amble around this family-friendly area's riverfront or attend a sporting event.
Long Beach
Why not spend a lazy afternoon at Long Beach during your trip to Calvert Beach-Long Beach?
Perigeaux Vineyards and Winery
4.0/10 (2 reviews)
You can enjoy a tasting or tour at Perigeaux Vineyards and Winery during your travels to St. Leonard. Amble around this family-friendly area's riverfront or attend a sporting event.
Flag Harbor Marina
Explore the waterfront in Calvert Beach-Long Beach with a trip to Flag Harbor Marina.
St. Leonard Hotel Deals
Historic 1825 Chesapeake Farm Stay
1380 Wagner Street St. Leonard MD
Fully refundableReserve now, pay when you stay
$141 nightly
$157 total
Nov 11 - Nov 12
Total with taxes and fees
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
St Leonard MD
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
$132 nightly
$146 total
Oct 21 - Oct 22
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
"Beautiful property on the Chesapeake Bay. It was very clean. We went off season highly recommend."
Reviewed on Oct 11, 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.
Find the Best St. Leonard Vacation Packages
St. Leonard Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 740 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | Running Hare Vineyard, Jefferson Patterson Park and Museum and Perigeaux Vineyards and Winery |
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Frequently asked questions
What's included in a St. Leonard vacation package?
A St. Leonard vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Given St. Leonard's focus on its scenic coastline, beach packages here often include convenient beach access. Many properties also offer amenities like airport transfers to and from Washington, DC (DCA-Ronald Reagan Washington National) and free breakfast, which can enhance your stay.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a St. Leonard vacation package?
When you bundle, you can save up to 30%*. To save money on a St. Leonard package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Is St. Leonard better suited for a beach vacation or a cultural trip?
St. Leonard is primarily an outdoor and nature destination, making it an excellent choice for a beach vacation. Its coastline along the Chesapeake Bay offers several inviting spots, such as Matoaka Beach, about 3 miles from the center, and Breezy Point Beach, about 4 miles away, which are popular for swimming and relaxation. Nature enthusiasts can also explore Calvert Cliffs State Park, about 8 miles from central St. Leonard, known for its fossil hunting and hiking trails.While beaches and outdoor activities are the main draw for a St. Leonard vacation, the area also offers some cultural and historical insights. Travelers can visit the Jefferson Patterson Park and Museum, located about 2 miles from central St. Leonard, which features archaeological sites and exhibits on local history. Overall, St. Leonard works best for those seeking a blend of coastal relaxation and natural exploration, with opportunities for historical discovery.
What are the top things to do in St. Leonard?
A St. Leonard vacation offers a variety of outdoor activities, from beach relaxation to historical exploration:Browse and book things to do in St. Leonard on Expedia.
Do you need to rent a car in St. Leonard, or is public transport enough?
For a St. Leonard vacation package, renting a car is highly recommended to fully explore the area. As an outdoor and nature destination primarily known for its beaches, St. Leonard has many spread-out attractions. For instance, Calvert Cliffs State Park is about 8 miles from central St. Leonard, and Matoaka Beach is about 3 miles away, making personal transportation essential for convenient access.A rental car provides the flexibility to visit various beaches, parks, and historical sites at your own pace, which is ideal for those planning a St. Leonard beach vacation. This means you can easily reach all the scenic spots and enjoy a comprehensive St. Leonard vacation package with flights.
Can I change or cancel my St. Leonard vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking St. Leonard vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later St. Leonard vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your St. Leonard vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to St. Leonard?
To find last-minute vacation packages to St. Leonard, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on St. Leonard vacation packages?
Free cancellation on a St. Leonard vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a St. Leonard vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your St. Leonard getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my St. Leonard vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
