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Tilghman Vacations

Pack those stellar shades. We have Tilghman 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 Tilghman – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Tilghman 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 Tilghman

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 Tilghman 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 Tilghman well.

Tilghman Flight + Hotel packages

Top Hotel Deals

See all 79 Properties in Tilghman
Black Walnut Point Inn

Black Walnut Point Inn

4417 Black Walnut Point Road, Tilghman
    3.5 out of 5.0
     
     

    Situated by the sea, this bed & breakfast is 2.7 mi (4.4 km) from Tilghman Watermen’s Museum and within 20 mi (32 km) of Chesapeake Bay Maritime Museum and St. ...

    Black Walnut Point Inn$165

    Black Walnut Point Inn$165
    Knapps Narrows Marina & Inn

    Knapps Narrows Marina & Inn

    6176 Tilghman Island Road, Tilghman
      3.0 out of 5.0
       
       

      Situated near the bay, this hotel is 0.8 mi (1.3 km) from Tilghman Watermen’s Museum and within 16 mi (25 km) of Chesapeake Bay Maritime Museum and St. Michaels ...

      Knapps Narrows Marina & Inn$170

      Knapps Narrows Marina & Inn$170
      Chesapeake House Tilghman Island

      Chesapeake House Tilghman Island

      21551 Chesapeake House Drive, Tilghman
        3.0 out of 5.0
         
         

        Situated on the waterfront, this hotel is 0.1 mi (0.2 km) from Tilghman Watermen’s Museum and within 16 mi (25 km) of Chesapeake Bay Maritime Museum and St. ...

        Lazyjack Inn on Dogwood Harbor

        Lazyjack Inn on Dogwood Harbor

        5907 Tilghman Island Road, Tilghman
          3.5 out of 5.0
           
           

          Situated on the waterfront, this bed & breakfast is 0.8 mi (1.4 km) from Tilghman Watermen’s Museum and within 16 mi (25 km) of Chesapeake Bay Maritime Museum ...

          Lazyjack Inn on Dogwood Harbor$185

          Lazyjack Inn on Dogwood Harbor$185
          Wylder Hotel Tilghman Island

          Wylder Hotel Tilghman Island

          21551 Chesapeake House Dr, Tilghman Island
             
             
            St Michaels Inn

            St Michaels Inn

            1228 S Talbot Street, St. Michaels
              2.5 out of 5.0
               
               

              Situated in the historical district, this hotel is within 2 mi (3 km) of St. Michaels Winery, St. Michaels Museum, and Chesapeake Bay Maritime Museum. Avalon ...

              St Michaels Inn$86

              St Michaels Inn$86
              Best Western Kent Narrows Inn

              Best Western Kent Narrows Inn

              3101 Main Street, Grasonville
                2.5 out of 5.0
                 
                 

                Situated in Grasonville, this motel is 1.1 mi (1.7 km) from Kent Island and within 12 mi (20 km) of Queenstown Premium Outlets and Chesapeake Bay Bridge. Sandy ...

                Best Western Kent Narrows Inn$97

                Best Western Kent Narrows Inn$97
                Hyatt Regency Chesapeake Bay

                Hyatt Regency Chesapeake Bay

                100 Heron Blvd, Cambridge
                  4.0 out of 5.0
                   
                   

                  Located in Cambridge, this beachfront resort is in the historical district and within 3 mi (5 km) of Dorchester County Visitors Center, Long Wharf Park, and ...

                  Hyatt Regency Chesapeake Bay$229

                  Hyatt Regency Chesapeake Bay$229
                  Sleep Inn Grasonville

                  Sleep Inn Grasonville

                  101 Vfw Ave, Grasonville
                    2.5 out of 5.0
                     
                     

                    Situated in Grasonville, this hotel is 2.5 mi (4.1 km) from Chesapeake Bay Environmental Center and within 6 mi (10 km) of Kent Island and Queenstown Harbor ...

                    Sleep Inn Grasonville$90

                    Sleep Inn Grasonville$90
                    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

                      Top Flight Deals

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