Leonardtown Holidays

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Things to do in and around Leonardtown

Leonardtown offers an array of outdoor activities perfect for adventure seekers and nature lovers. Visitors can enjoy thrilling motor racing, explore scenic recreational areas, and partake in educational experiences. Don't miss the opportunity to take boat tours that showcase the beautiful surroundings and provide a unique perspective of this charming town.

Shopping

In Leonardtown, you can explore The Shoppes at McIntosh for a variety of shops, or visit Wildewood Shopping Center, located 9.7km away, for family-friendly vibes. If you're up for a drive, Cecil's Old Mill, situated 12.9km away, offers unique finds to take home.

Recreation

At Breton Bay Golf Course, enjoy a round of golf amidst lush greenery and serene landscapes, perfect for both relaxation and sport. For a tranquil escape, visit Elms Beach Park, where you can unwind by the water, surrounded by nature. R&J's PlayPark offers family-friendly mini-golf for an adventurous day out.

Adventure

Experience the thrills of Chesapeake Beach Water Park, 45.1km from Leonardtown, with exhilarating water slides and family fun. For speed enthusiasts, Maryland International Raceway, 20.9km away, offers adrenaline-pumping races. Stroll along Solomons Island Boardwalk, 16.1km distant, enjoying romantic beach views and outdoor charm.

Nightlife

For a delightful evening, consider catching a performance at the Port Tobacco Players theatre, located 40.2km from Leonardtown. This venue offers a charming mix of romance, entertainment, and cultural vibes, perfect for an engaging night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Leonardtown

Leonardtown offers a delightful blend of outdoor adventures and scenic beauty, making it an ideal destination for those seeking both family-friendly and urban experiences. Visitors can explore a variety of attractions, including urban parks and national state parks, all designed to enhance your enjoyment of nature and local culture. Whether you're chasing thrills or simply wishing to unwind, Leonardtown has something to cater to every traveller's desire.

  • St. Mary's River State Park: Experience the great outdoors with stunning scenery and adventure opportunities at St. Mary's River State Park, located 8.0km from Leonardtown. Enjoy hiking, birdwatching, and picnicking amid the lush landscapes and winding waterways.
  • Leonardtown Town Hall: Situated within Leonardtown, the Town Hall showcases the town's rich history and serves as a hub for local governance. Its charming architecture and welcoming atmosphere make it a great spot to learn about the community's heritage.
  • Leonardtown Park: A perfect family-friendly destination, Leonardtown Park offers eco-friendly spaces for outdoor activities. Enjoy playgrounds, walking trails, and picnic areas, all set in a serene environment that encourages relaxation and connection with nature.

Best time to go to Leonardtown

The best time to visit Leonardtown is dependent 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.7°F (2.6°C)Light RainMostly SunnySlightly LowSlightly Low
February39.4°F (4.1°C)Light RainMostly SunnyAverageSlightly Low
March45.9°F (7.7°C)Light RainMostly SunnySlightly HighAverage
April56.1°F (13.4°C)Light RainMostly SunnySlightly HighAverage
May65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
June73.6°F (23.1°C)Light RainMostly SunnyAverageSlightly High
July78.6°F (25.9°C)Light RainMostly SunnySlightly HighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyAverageSlightly High
September71.1°F (21.7°C)Light RainMostly SunnyAverageAverage
October60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
November49.3°F (9.6°C)Light RainMostly SunnySlightly LowAverage
December42.4°F (5.8°C)Light RainMostly SunnySlightly LowSlightly Low

Booking tips and Expedia advantages for Leonardtown

For an economical visit to Leonardtown, consider travelling between December and February when accommodation prices are lower, avoiding the pricier summer months. Booking your stay on a Monday can also save you money compared to Saturday, the most expensive day. Use Expedia's search tool to filter by budget and eco-friendly options for sustainable stays. Additionally, combining your hotel, flights, and activities into a package can yield significant savings. Lastly, sorting accommodation prices from lowest to highest will help you find the best deals available.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Leonardtown are December to February, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Leonardtown is Monday. The most expensive day to stay in Leonardtown is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To discover the best prices and deals, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially reduce your expenses by combining your hotel reservation in Leonardtown with your flights and activities through an Expedia package.

Top hotels in Leonardtown

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
Fully refundable
The price is Rp2.232.878 per night from 23 Nov to 24 Nov
Rp2.232.878
Rp2.478.495 total
23 Nov - 24 Nov
includes taxes & fees
9.2/10 Wonderful! (152 reviews)
Overall 10/10. Convenient area and nice building and room.

Reviewed on 18 Oct 2025

The Inn at Leonardtown, an Ascend Collection Hotel
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is Rp1.781.180 per night from 25 Nov to 26 Nov
Rp1.781.180
Rp1.977.110 total
25 Nov - 26 Nov
includes taxes & fees
7.8/10 Good! (949 reviews)
Great place, I would stay again.

Reviewed on 26 Oct 2025

Solomons Inn Resort & Marina
My Place Hotel - Dahlgren/King George, VA

My Place Hotel - Dahlgren/King George, VA

2.5 out of 5
4235 Market Center Drive, King George, VA
Fully refundableReserve now, pay when you stay
The price is Rp1.386.776 per night from 30 Nov to 1 Dec
Rp1.386.776
Rp1.529.615 total
30 Nov - 1 Dec
includes taxes & fees
9.4/10 Exceptional! (616 reviews)
Great Staff I would recommend to anyone who wants a long-term stays or just for a weekend.

Reviewed on 30 Oct 2025

My Place Hotel - Dahlgren/King George, VA
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.