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Check prices for these dates, 15 – 16 December 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.
Rating: 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.
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.
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.
Explore the great outdoors at Abell's Wharf, a lovely green space in Leonardtown. Take in the festivals and sunsets in the area.
Enjoy an outing to Saint Mary's Fairground during your stay in Leonardtown. Take in the festivals and sunsets in the area.
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.
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.
Leonard's Grant Community Area is just one of the places to see in Leonardtown, so why not enjoy the other things to explore during your travels? Take in the festivals and sunsets in the area.
Explore the historic waterfront square where local artisans showcase their crafts and restaurants serve fresh Chesapeake Bay seafood. Kayak along Breton Bay's peaceful waters or visit the nearby Patuxent River Naval Air Museum in Lexington Park.
Discover a delightful range of accommodations in Leonardtown, Maryland, where hospitality meets comfort. Whether you prefer a charming bed and breakfast or a modern hotel, you'll find options that cater to business travellers and offer pet-friendly and LGBTQIA-friendly experiences. Explore the best hotels in Leonardtown, MD, and enjoy a warm welcome during your visit to this picturesque town.
Leonardtown, Maryland, offers a delightful blend of outdoor adventure and charming scenery for travellers. Discover the family-friendly atmosphere of downtown Leonardtown, where you can explore local shops and savour delectable cuisine. Nearby attractions provide opportunities for recreation and excursions, allowing visitors to connect with friendly locals and experience the vibrant community spirit. Whether you're seeking relaxation or adventure, Leonardtown and its surroundings promise an unforgettable holiday experience.
Leonardtown, Maryland, is an ideal destination for outdoor enthusiasts, offering stunning scenery and adventurous activities. Visitors can enjoy a variety of recreational areas, indulge in thrilling motor racing experiences, and engage in educational pursuits that enhance their trip. With its charming atmosphere and array of attractions, Leonardtown promises a delightful getaway for those seeking both adventure and relaxation.
Shopping
For a delightful shopping experience in Leonardtown, visit The Shoppes at McIntosh, which offers a vibrant mix of city, family, and business vibes. Wildewood Shopping Center, 3.7km away, also provides a great selection. If you're up for a drive, Cecil's Old Mill is 5.0km away, featuring unique gifts.
Recreation
At Breton Bay Golf Course, enjoy a serene golfing experience amidst lush landscapes, perfect for relaxation and sport. Elms Beach Park, located 9.9km away, offers a tranquil setting for unwinding by the water. R&J's PlayPark, 10.6km away, provides a fun-filled mini golf adventure for families.
Adventure
Experience thrilling races at Maryland International Raceway, located 8.1km from Leonardtown, where adrenaline meets speed. For family fun, head to Chesapeake Beach Water Park, 17.4km away, offering exciting water slides and pools. Alternatively, enjoy the exhilarating atmosphere at Budds Motorcross Speedway, also 8.1km distant.
Nightlife
For a delightful evening, catch a performance at the Port Tobacco Players theatre, located 15.5km from Leonardtown. This venue offers a charming blend of entertainment and culture, perfect for families or a romantic night out.
For a budget-friendly trip to Leonardtown, consider visiting between December and February for lower accommodation rates, with Monday being the cheapest day to stay. Avoid weekends, particularly Saturday, when prices peak. Use Expedia's search tool to compare hotel deals and filter by price to find the best offers. Look into package deals that combine your hotel, flights, and activities to save even more. Additionally, take advantage of free local attractions to enhance your experience without straining your wallet.
Leonardtown, Maryland, offers a delightful mix of outdoor adventures and scenic beauty, making it perfect for a family getaway or a city experience. Visitors can explore attractions such as the Leonardtown Wharf, Leonardtown Winery Park, and local historic lighthouses. With its stunning urban parks and state parks, Leonardtown invites you to enjoy nature while discovering popular local sites and activities during your stay.
The best time to visit Leonardtown is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.
| Calendar Month | Temperature | Precipitation | Cloudiness | Occupancy | Pricing |
| January | 36.7°F (2.6°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
| February | 39.4°F (4.1°C) | Light Rain | Mostly Sunny | Average | Slightly Low |
| March | 45.9°F (7.7°C) | Light Rain | Mostly Sunny | Slightly High | Average |
| April | 56.1°F (13.4°C) | Light Rain | Mostly Sunny | Slightly High | Average |
| May | 65.1°F (18.4°C) | Light Rain | Mostly Sunny | Average | Average |
| June | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Average | Average |
| July | 78.6°F (25.9°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High |
| August | 76.8°F (24.9°C) | Light Rain | Mostly Sunny | Average | Slightly High |
| September | 71.1°F (21.7°C) | Light Rain | Mostly Sunny | Average | Average |
| October | 60.8°F (16.0°C) | Light Rain | Mostly Sunny | Average | Average |
| November | 49.3°F (9.6°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly High |
| December | 42.4°F (5.8°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
To reach Leonardtown, Maryland, you can fly into two major airports. Ronald Reagan Washington National Airport (DCA) is situated 27.3km away, with nearby luxury hotels such as Salamander Washington DC, InterContinental Washington D.C. - The Wharf, and Sofitel Washington DC Lafayette Square, all offering convenient access to the airport. Alternatively, Salisbury - Ocean City Wicomico Regional Airport (SBY) is located 37.9km from Leonardtown, with options like Country Inn & Suites by Radisson, Courtyard by Marriott, and Residence Inn by Marriott, providing comfortable stays and accessibility to the airport. Both airports offer various transportation services for seamless travel.
The best area to stay in Leonardtown is the historic downtown area, particularly around Washington Street and Fenwick Street.
This charming part of town is the heart of Leonardtown, offering a relaxed pace and easy access to local amenities. You'll find a collection of independent shops, art galleries, and eateries, many housed in beautifully preserved historic buildings. The Leonardtown Wharf, with its scenic boardwalk along Breton Bay, is a central feature, great for a leisurely stroll.
Couples looking for a peaceful getaway will particularly enjoy this area. The historic streets provide a pleasant backdrop for exploring, and there are several cosy restaurants and wine bars great for an evening out. The proximity to the waterfront adds a romantic touch, especially watching the sunset over the bay.
For solo travellers or those on a business trip who appreciate convenience and local character, staying downtown is also ideal.
For a highly recommended hotel in Leonardtown, The Inn at Leonardtown, an Ascend Collection Hotel, consistently receives positive feedback from travellers.
This 9.2-rated hotel is praised for its spacious and clean rooms, as well as its tasty breakfast. Guests also highlight its great location within the historical district and the friendly staff. The hotel provides amenities such as air conditioning, designer toiletries, and free self-parking, including accessible and van parking options. It is conveniently located just 0.7 km from Leonardtown Park and 1.9 km from Saint Mary's County Library Leonardtown Branch.
For a highly-rated budget hotel in Leonardtown, The Inn at Leonardtown, an Ascend Collection Hotel, is an excellent choice.
This hotel boasts a superb 9.2 review rating, with guests frequently praising its spacious and clean rooms, tasty breakfast, and friendly staff. It offers complimentary WiFi, free self-parking, and accessible parking options. The hotel is conveniently located just 1.5 km from Miedzinski Park and 1.9 km from Saint Mary's County Library Leonardtown Branch.
For a highly-rated hotel in Leonardtown near Leonardtown Park, The Inn at Leonardtown, an Ascend Collection Hotel, is an excellent choice.
This hotel, with an impressive 9.2 rating, is conveniently located just 0.7 km from Leonardtown Park. Guests consistently praise its spacious and clean rooms, the tasty breakfast, and the friendly staff. It offers complimentary WiFi, free toiletries, and free self-parking, including accessible and van parking options.
The best times to go to Leonardtown are during the spring (late April to early June) and autumn (September to late October) when the weather is most pleasant for outdoor activities and exploring the town.
During spring, the temperatures are mild, typically ranging from 15°C to 25°C, and the local flora is in full bloom, making it ideal for walks along the waterfront or visiting the nearby farms and vineyards. This season also sees fewer crowds than the peak summer months, allowing for a more relaxed experience.
Autumn brings comfortable temperatures, generally between 10°C and 20°C, along with the scenic beauty of changing leaves, particularly in the surrounding countryside. This period is excellent for enjoying local harvest festivals and outdoor markets without the humidity of summer. It's also a good time for couples to enjoy a quiet getaway, perhaps exploring the historic downtown and its independent shops.
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Leonardtown.
Prices for hotels in Leonardtown often vary, but you can find a great deal from £63 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.