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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 64 Hotels 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, Cecil's Old Mill, and Sotterley Plantation. Greenwell ...

    Executive Inn & Suites Park Avenue$152

    Executive Inn & Suites Park Avenue$152
    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$93

      Comfort Inn & Suites$93
      Red Roof Inn California, MD - NAVAIR

      Red Roof Inn 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 Patuxent River Naval Air Museum, Drum Point Lighthouse, and Patuxent River Naval Air Station. Sotterley ...

        Red Roof Inn California, MD - NAVAIR$67

        Red Roof Inn California, MD - NAVAIR$67
        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 within 6 mi (10 km) of Patuxent River Naval Air Museum, Drum Point Lighthouse, and Patuxent River Naval Air Station. Annmarie ...

          Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD$95

          Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD$95
          Super 8 Lexington Prk Ca Area

          Super 8 Lexington Prk Ca 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 Lexington Prk Ca Area$48

            Super 8 Lexington Prk Ca Area$48
            Island Inn & Suites, an Ascend Hotel Collection Member

            Island Inn & Suites, an Ascend Hotel Collection Member

            16810 Piney Point Road, Piney Point
              3.0 out of 5.0
               
               

              Located in the heart of Piney Point, this hotel is 2.7 mi (4.4 km) from Piney Point Lighthouse and within 12 mi (20 km) of Dennis Point Marina and Cecil's Old ...

              Island Inn & Suites, an Ascend Hotel Collection Member$89

              Island Inn & Suites, an Ascend Hotel Collection Member$89
              Quality Inn Solomons - Beacon Marina

              Quality Inn Solomons - Beacon Marina

              255 Lore Rd, Solomons
                2.5 out of 5.0
                 
                 

                Situated in Solomons, this hotel is 0.1 mi (0.1 km) from Drum Point Lighthouse and 1.9 mi (3.1 km) from Annmarie Sculpture Garden and Arts Center. Cove Point ...

                Quality Inn Solomons - Beacon Marina$85

                Quality Inn Solomons - Beacon Marina$85
                Holiday Inn Express Prince Frederick

                Holiday Inn Express Prince Frederick

                355 Merrimac Ct, Prince Frederick
                  2.5 out of 5.0
                   
                   

                  Situated near the beach, this hotel is 3.4 mi (5.4 km) from Running Hare Vineyard and within 12 mi (20 km) of Breezy Point Beach and Jefferson Patterson Park ...

                  Holiday Inn Express Prince Frederick$94

                  Holiday Inn Express Prince Frederick$94
                  Holiday Inn Express & Suites Lexington Park-California

                  Holiday Inn Express & Suites Lexington Park-California

                  45260 Abell House Lane, California
                    2.5 out of 5.0
                     
                     

                    Located in the heart of California, this hotel is 3.1 mi (5 km) from Patuxent River Naval Air Museum and within 6 mi (10 km) of Patuxent River Naval Air Station ...

                    Holiday Inn Express & Suites Lexington Park-California$108

                    Holiday Inn Express & Suites Lexington Park-California$108
                    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 within 12 mi (20 km) of Breezy Point Beach and Jefferson ...

                      Springhill Suites by Marriott Prince Frederick$98

                      Springhill Suites by Marriott Prince Frederick$98

                      Top Flight Deals

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