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Leonardtown Vacations

Pack those stellar shades. We have Leonardtown vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Leonardtown – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Leonardtown vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Leonardtown

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Leonardtown vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Leonardtown well.

Top Hotel Deals

See all 67 Properties in Leonardtown
Executive Inn & Suites Park Avenue

Executive Inn & Suites Park Avenue

41655 Park Avenue, Leonardtown
    2.5 out of 5.0
     
     

    Located in the heart of Leonardtown, this hotel is within 9 mi (15 km) of St. Mary's River State Park, Sotterley Plantation, and Cecil's Old Mill. Greenwell ...

    Executive Inn & Suites Park Avenue$152

    Executive Inn & Suites Park Avenue$152
    Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD

    Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD

    44941 Worth Ave, California
      2.5 out of 5.0
       
       

      Situated in California, this hotel is 2.9 mi (4.7 km) from St. Mary's River State Park and within 6 mi (10 km) of Patuxent River Naval Air Museum and Drum Point ...

      Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD$87

      Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD$87
      La Quinta Inn & Suites Lexington Park - Patuxent

      La Quinta Inn & Suites Lexington Park - Patuxent

      22769 Three Notch Rd, California
        2.5 out of 5.0
         
         

        Situated in California, this hotel is 2.1 mi (3.4 km) from Patuxent River Naval Air Museum and within 6 mi (10 km) of Patuxent River Naval Air Station and Cecil's ...

        La Quinta Inn & Suites Lexington Park - Patuxent$72

        La Quinta Inn & Suites Lexington Park - Patuxent$72
        Springhill Suites by Marriott Prince Frederick

        Springhill Suites by Marriott Prince Frederick

        75 Sherry Lane, Prince Frederick
          3.0 out of 5.0
           
           

          Situated in Prince Frederick, this condo building is 3.4 mi (5.4 km) from Running Hare Vineyard and 10.9 mi (17.6 km) from Breezy Point Beach. Chesapeake Beach ...

          Springhill Suites by Marriott Prince Frederick$98

          Springhill Suites by Marriott Prince Frederick$98
          Extended Stay America Lexington Park - Pax River

          Extended Stay America Lexington Park - Pax River

          46565 Expedition Dr, Lexington Park
            2.5 out of 5.0
             
             

            Situated in Lexington Park, this hotel is 0.3 mi (0.5 km) from Patuxent River Naval Air Museum and 1.3 mi (2.1 km) from Patuxent River Naval Air Station. Cecil's ...

            Extended Stay America Lexington Park - Pax River$63

            Extended Stay America Lexington Park - Pax River$63
            Super 8 by Wyndham Lexington Park/California Area

            Super 8 by Wyndham Lexington Park/California Area

            22801 Three Notch Rd, California
              2.0 out of 5.0
               
               

              Situated in California, this hotel is 2.2 mi (3.5 km) from Patuxent River Naval Air Museum and within 6 mi (10 km) of Patuxent River Naval Air Station and Cecil's ...

              Super 8 by Wyndham Lexington Park/California Area$49

              Super 8 by Wyndham Lexington Park/California Area$49
              Country Inn & Suites by Radisson, Dahlgren, VA

              Country Inn & Suites by Radisson, Dahlgren, VA

              4755 James Madison Pkwy, King George
                3.0 out of 5.0
                 
                 

                Situated in King George, this hotel is 5.8 mi (9.3 km) from Aqualand Marina and 6.9 mi (11.1 km) from Caledon State Park. James Monroe Birthplace and Saint Ignatius ...

                Country Inn & Suites by Radisson, Dahlgren, VA$101

                Country Inn & Suites by Radisson, Dahlgren, VA$101
                Comfort Inn & Suites

                Comfort Inn & Suites

                21885 Three Notch Rd, Lexington Park
                  2.5 out of 5.0
                   
                   

                  Situated on the Strip, this hotel is within a 15-minute walk of Patuxent River Naval Air Station and Patuxent River Naval Air Museum. Cecil's Old Mill and St. ...

                  Comfort Inn & Suites$92

                  Comfort Inn & Suites$92
                  Red Roof Inn & Suites California, MD - NAVAIR

                  Red Roof Inn & Suites California, MD - NAVAIR

                  23428 Three Notch Rd, California
                    2.0 out of 5.0
                     
                     

                    Situated in California, this hotel is within 6 mi (10 km) of St. Mary's River State Park, Patuxent River Naval Air Museum, and Drum Point Lighthouse. Patuxent ...

                    Red Roof Inn & Suites California, MD - NAVAIR$63

                    Red Roof Inn & Suites California, MD - NAVAIR$63
                    Hilton Garden Inn Solomons

                    Hilton Garden Inn Solomons

                    13100 Dowell Road, Solomons
                      3.0 out of 5.0
                       
                       

                      This family-friendly Solomons hotel is located in a rural location, within 2 mi (3 km) of Annmarie Sculpture Garden and Arts Center and Drum Point Lighthouse. ...

                      Hilton Garden Inn Solomons$101

                      Hilton Garden Inn Solomons$101

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.