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Chesapeake Beach Vacations

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

Hotwire can help you find your travel bliss with Chesapeake Beach 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 Chesapeake Beach

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 Chesapeake Beach 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 Chesapeake Beach well.

Top Hotel Deals

See all 74 Hotels in Chesapeake Beach
Chesapeake Beach Resort And Spa

Chesapeake Beach Resort And Spa

4165 Mears Ave, Chesapeake Beach
    3.0 out of 5.0
     
     

    Situated on the waterfront, this spa hotel is within 32 mi (52 km) of Prince George's Community College, Six Flags America, and Maryland State House. William ...

    Chesapeake Beach Resort And Spa$109

    Chesapeake Beach Resort And Spa$109
    Colony South Hotel & Conference Center

    Colony South Hotel & Conference Center

    7401 Surratts Rd, Clinton
      3.0 out of 5.0
       
       

      Situated in the suburbs, this spa hotel is within 12 mi (20 km) of The Theater, Robert F. Kennedy Stadium, and Anacostia Museum. Show Place Arena and Fort Dupont ...

      Colony South Hotel & Conference Center$81

      Colony South Hotel & Conference Center$81
      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
        Extended Stay America Annapolis - Womack Drive

        Extended Stay America Annapolis - Womack Drive

        1 Womack Dr, Annapolis
          2.5 out of 5.0
           
           

          Situated in Annapolis, this hotel is 1.7 mi (2.7 km) from Westfield Annapolis Mall and 2.1 mi (3.3 km) from Anne Arundel Medical Center. Maryland State House ...

          Extended Stay America Annapolis - Womack Drive$81

          Extended Stay America Annapolis - Womack Drive$81
          Econo Lodge Andrews Air Force Base

          Econo Lodge Andrews Air Force Base

          7851 Malcolm Road, Clinton
            2.0 out of 5.0
             
             

            Located in the heart of Clinton, this hotel is within 12 mi (20 km) of Tanger Outlets, Robert F. Kennedy Stadium, and Nationals Park. Arena Stage and Lyceum ...

            Econo Lodge Andrews Air Force Base$62

            Econo Lodge Andrews Air Force Base$62
            Residence Inn by Marriott Annapolis

            Residence Inn by Marriott Annapolis

            170 Admiral Cochrane Dr, Annapolis
              3.0 out of 5.0
               
               

              Situated in the business district, this hotel is 1.4 mi (2.3 km) from Westfield Annapolis Mall and 1.9 mi (3 km) from Anne Arundel Medical Center. Maryland State ...

              Residence Inn by Marriott Annapolis$110

              Residence Inn by Marriott Annapolis$110
              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
                Holiday Inn Express Waldorf

                Holiday Inn Express Waldorf

                11370 Days Ct, Waldorf
                  2.5 out of 5.0
                   
                   

                  Located in the heart of Waldorf, this hotel is 0.9 mi (1.4 km) from St. Charles Towne Center and within 6 mi (10 km) of White Plains Golf Course and Regency ...

                  Holiday Inn Express Waldorf$99

                  Holiday Inn Express Waldorf$99
                  SpringHill Suites by Marriott Annapolis

                  SpringHill Suites by Marriott Annapolis

                  189 Admiral Cochrane Drive, Annapolis
                    3.0 out of 5.0
                     
                     

                    Situated in Annapolis, this hotel is 1.7 mi (2.7 km) from Westfield Annapolis Mall and 2.1 mi (3.3 km) from Anne Arundel Medical Center. Maryland State House ...

                    SpringHill Suites by Marriott Annapolis$89

                    SpringHill Suites by Marriott Annapolis$89
                    La Quinta Inn Waldorf

                    La Quinta Inn Waldorf

                    11770 Business Park Dr, Waldorf
                      2.5 out of 5.0
                       
                       

                      Situated in the suburbs, this hotel is 2.9 mi (4.6 km) from St. Charles Towne Center and within 9 mi (15 km) of White Plains Golf Course and Regency Furniture ...

                      La Quinta Inn Waldorf$72

                      La Quinta Inn Waldorf$72

                      Top Flight Deals

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