Leonardtown Holidays
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Your Leonardtown Holiday
The rich history and coastal scenery are just the start of the things Leonardtown has to offer. Discover the best parts of this captivating city your way with a customised Leonardtown holiday package. A trip to Leonardtown is a terrific opportunity to see the sights. Be sure to look around big-name attractions such as St. Marys River State Park, Port of Leonardtown Winery and New Towne Neck State Park. Whoever you're travelling with and whatever your bank balance, your ultimate Leonardtown holiday is just a few clicks away with Expedia.
Leonardtown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,600 |
Max Temp Winter | 7ºC |
Max Temp Summer | 29ºC |
Top Sights | St. Marys River State Park, St. Clements Island State Park and Jefferson Patterson Park and Museum |
Top hotels in Leonardtown
The Inn at Leonardtown, an Ascend Collection Hotel
41655 Park Avenue Leonardtown MD
Fully refundable
£120
1 Nov - 2 Nov
includes taxes & fees
9.4/10 Exceptional! (190 reviews)
"Welcoming staff, excellently situated in Downtown Leonardtown, decent offering of complimentary breakfast, including pre-made filled croissants. Only issue was my initial room suffered from external noise issues, suspected to be from the hotels air conditioning system (not the room), however the ..."
Reviewed on 23 Sept 2026
avid hotel California - Lexington Park by IHG
23274 Three Notch Road California MD
Fully refundable
£81
14 Oct - 15 Oct
includes taxes & fees
River Edge Inn
30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
£67
11 Oct - 12 Oct
includes taxes & fees
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
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.
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.
Leonardtown Library
This community hub offers extensive book collections and digital resources in a welcoming environment. Explore the library's diverse educational programmes or reserve a meeting room for collaborative projects.
Saint Mary's Fairground
Enjoy an outing to Saint Mary's Fairground during your stay in 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.
Leonardtown Park
This waterfront park on Breton Bay blends history with modern recreation in a serene setting. Enjoy kayaking, sunset strolls along the boardwalk, or attend seasonal events like the Water's Edge Music Series.
Frequently asked questions
Why should I book my Leonardtown holiday with Expedia?
Choose Expedia to organise your next escape simply and all in the same place. Our top tip for getting a great deal on a Leonardtown getaway? Bundle your flights, hotel and/or car hire into a package holiday. Then throw in a couple of exciting tours and activities. Many bookings also include flexible cancellation policies, so there's no need to panic if you have to change plans. Round-the-clock help with making tweaks to your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Leonardtown?
If you love the excitement that comes with peak season, head to Leonardtown in June, October and November. If you'd like a calmer vibe, January, February and August will suit you better. With average daytime temperatures of 2ºC, January is the coolest period in Leonardtown. The warmest month is July, when you can experience average temperatures of 25ºC during the day. Whatever the weather conditions, you'll find plenty of things to keep you busy here.
What is the top hotel for my holiday in Leonardtown?
Offering many of home's creature comforts, Courtyard by Marriott Baltimore Downtown/McHenry Row will make the ideal base for your Leonardtown getaway.
How do I get a cheap holiday to Leonardtown?
Our Leonardtown holidays mean plenty of savings for the savvy traveller. For the best deals, simply bundle your hotel, flights and extras (including activities). But bargain prices are only the start of your next memorable adventure. When you book with Expedia, you'll have more than 400 airlines and 321,000 hotel options around the world to pick from. No matter your style or budget, there's a holiday here just for you. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Leonardtown holiday?
Ensure your holiday in Leonardtown is an unforgettable one by checking out its top attractions. St. Marys River State Park, Sotterley Plantation, Cecils Old Mill and Port of Leonardtown Winery are some of the things worth seeing while you're here.
What is the best area to stay in when on holiday in Leonardtown?
A getaway to Leonardtown isn't complete without paying a visit to Port of Leonardtown Winery. Why not book a stay close to this fantastic tourist attraction?
Do I need a visa for my Leonardtown holiday?
Official government websites are the best source of information on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for holidays or business, will determine if you'll need a visa for Leonardtown. Be sure that your passport is up to date and has a minimum of six months validity remaining beyond your return date. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Leonardtown holiday?
Though everyone's fashion style differs, it can help to have a few guidelines for what type of clothes to wear on your holiday in Leonardtown. Consider browsing social media before you go to get inspiration for local fashion trends. Pack with confidence by checking the forecast in Leonardtown. July brings the warmest temperatures, with daily averages of 25ºC, while January days average 2ºC, making it the coolest time of the year.
What does an Expedia Leonardtown holiday include?
Flights, car hires and hotels, or any combination of them — the choice is yours. Whether you're exploring Leonardtown on a family road trip or adventuring with your friends, there's a bundle to match your style and budget. Once you've made your booking, why not add on some tours or activities? Expedia features different kinds of properties, with the most popular in Leonardtown including private holiday homes and apartments. With Expedia, you'll always enjoy the freedom and flexibility to tailor-make your holiday your way.
Does Expedia offer Book Now, Pay Later Leonardtown holidays?
Yes, we do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan best suited to your needs during checkout and take away the stress of budgeting for your trip. Make sure you bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:
- Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient instalment plans. If making bite-sized repayments each month works for you, pick this option during the checkout process.
- No-deposit holidays: When you want to jump on an incredible deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to get what you want.
Can I choose my airline with a Leonardtown Expedia holiday?
Most definitely. Expedia has more than 400 airline partners to pick from globally. With so much choice, finding the right carrier to bring you to Leonardtown will be easy.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
