Leonardtown Vacations from $289
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Your Leonardtown Vacation
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 customized Leonardtown vacation 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 traveling with and whatever your bank balance, your ultimate Leonardtown vacation is just a few clicks away with Expedia.
The Latest Leonardtown Vacation Packages
- Convention center Indoor free parking
Jan 12 - Jan 17Convention center Indoor free parking + Flight
Downtown Baltimore5 nights4.0 star propertyRoundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$446$289found 1 day agoper traveler - Eurostars Saint Gregory Dupont Circle Georgetown
Jan 20 - Jan 25Eurostars Saint Gregory Dupont Circle Georgetown + Flight
Downtown Washington D.C.5 nights4.0 star property8.6/10 - Excellent (1,004 reviews)Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - IAD • Nonstop BWI - ATL • Nonstop$686$373found 1 day agoper traveler - Sofitel Washington DC Lafayette Square
Jan 12 - Jan 17Sofitel Washington DC Lafayette Square + Flight
Downtown Washington D.C.5 nights5.0 star property9.0/10 - Wonderful (1,297 reviews)"Rather than a luxury hotel which was our expectation of Sofitel standards, this hotel needs an upgrade."Reviewed November 7, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$924$563found 1 day agoper traveler - Harbor free indoor parking
Jan 20 - Jan 25Harbor free indoor parking + Flight
Downtown Baltimore5 nights4.0 star propertyRoundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$567$347found 1 day agoper traveler - citizenM Washington DC NoMa
Jan 20 - Jan 25citizenM Washington DC NoMa + Flight
Northeast5 nights4.0 star property9.2/10 - Wonderful (3,005 reviews)"Centrally located near the train station and very clean with super helpful staff."Reviewed November 7, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - IAD • Nonstop BWI - ATL • Nonstop$485$310found 1 day agoper traveler
Where to stay in and around Leonardtown
California
Discover California, a welcoming destination perfectly suited for families and outdoor enthusiasts who will appreciate its stunning scenery and adventure opportunities. Enjoy activities at Calvert Cliffs State Park and unwind at the picturesque Harbor Island Marina or Willow Creek Gardens. With its vibrant recreational offerings, California makes for an excellent base to explore and experience. Located about 7 miles by car from Leonardtown, California is a smart choice for your next hotel booking.
Compton
Experience the charm of Compton, a delightful hub for families and weekend getaways looking to explore the attractions of Leonardtown. Visitors can enjoy the scenic beauty of Indian Village Archeological Park and New Towne Neck State Park, perfect for outdoor activities and leisurely strolls. With shopping centers nearby, Compton offers a well-rounded experience. Nestled in Leonardtown, this village is a smart choice for those seeking a blend of relaxation and adventure.
Loveville
Families and nature enthusiasts will love Loveville, known for its charming blend of outdoor activities and urban experiences. With attractions like the serene Former Rowland Property nature reserve, the Leonard's Grant Recreation Area urban park, and easy access to local motor racing events, Loveville offers a delightful weekend getaway. Located about 5 miles by car from Leonardtown, it provides a convenient base for exploring the area. Staying in Loveville makes for a smart choice for your vacation, ensuring both adventure and relaxation.
Hollywood
Immerse yourself in Hollywood, where families, couples, and adventure seekers can easily access stunning outdoor scenery and engaging activities. This charming city offers attractions like Calvert Cliffs State Park, perfect for hiking and enjoying breathtaking views, and the historic Sotterley Plantation for a glimpse into the past. With the Hollywood Soccer Complex nearby, there's something for everyone. Located about 6 miles by car from Leonardtown, Hollywood makes for a smart choice for your next getaway.
Clements
Travelers seeking a weekend getaway will find Clements to be the perfect base for their vacation, featuring a blend of nature, adventure, and local charm. Just a short drive from Leonardtown, Clements offers access to exciting activities like motor racing, shopping, and exploring the historic lighthouse. With its appealing outdoor spaces, including the Former Rowland Property and Leonard's Grant Recreation Area, visitors can immerse themselves in the area's natural beauty. Clements is a smart choice for your vacation, combining convenience and delightful experiences.
Discover the most popular places to visit in Leonardtown
Leonardtown Hotel Deals
The Inn at Leonardtown, an Ascend Collection Hotel
The Inn at Leonardtown, an Ascend Collection Hotel"A clean, pleasant hotel with lots of light and friendly staff in the middle of little Leonardtown. I actually asked the front desk if they were new because of how clean everything was and they said they did a major renovation about 5 years ago. Easy (and FREE) parking across the street. Our room (a king bed) was clean and quiet. If we're ever in the area again, this is where we'd stay."
Sleep Inn & Suites California MD
Sleep Inn & Suites California MD
avid hotel California - Lexington Park by IHG
avid hotel California - Lexington Park by IHG
Spark by Hilton California Lexington Park
Spark by Hilton California Lexington Park
Holiday Inn Express & Suites Lexington Park-California by IHG
Holiday Inn Express & Suites Lexington Park-California by IHG
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Hampton Inn by Hilton Lexington Park
Hampton Inn by Hilton Lexington Park"Breakfast was plentiful and mostly good. Staff was quite accommodating and friendly."
Super 8 by Wyndham Lexington Park/California Area
Super 8 by Wyndham Lexington Park/California AreaFrequently Asked Questions
How much does a Leonardtown vacation package cost?
You can grab a vacation package to this top destination from $289 on Expedia. But how much your vacation to Leonardtown costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Leonardtown?
You can typically find reduced prices and greater availability in January, February and August. Explore our cheap Leonardtown vacation packages and you could score some great off-season discounts.
How many days is enough for Leonardtown?
With a well-organized itinerary, you can easily hit the top Leonardtown sights in a handful of days. But if you prefer to venture off the beaten track or take day trips, think about booking your Leonardtown vacation for longer.
How to find the best Leonardtown package deals?
Finding a cheap Leonardtown package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Leonardtown package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Leonardtown vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and stays separately. Better still, you can personalize your Leonardtown getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Leonardtown?
Land fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Leonardtown trip.
Does Expedia offer Book Now, Pay Later Leonardtown vacation packages?
Your Leonardtown break is meant to be an escape from your busy life, not a source of money-related stress. So to give you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.