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Chesapeake City Vacations

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

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

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 City 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 City well.

Top Hotel Deals

See all 92 Hotels in Chesapeake City
Inn At The Canal Bed & Breakfast

Inn At The Canal Bed & Breakfast

104 Bohemia Avenue, Chesapeake City
    3.5 out of 5.0
     
     

    Situated in Chesapeake City, this bed & breakfast is 0.6 mi (0.9 km) from C and D Canal Museum and within 9 mi (15 km) of Back Creek Golf Club and Bohemia Vista ...

    Red Roof Inn & Suites Newark - University

    Red Roof Inn & Suites Newark - University

    1119 S College Avenue, Newark
      2.0 out of 5.0
       
       

      Situated in the business district, this hotel is within 1 mi (2 km) of Bob Carpenter Center and Fred Rust Ice Arena. University of Delaware and Pond Ice Arena ...

      Red Roof Inn & Suites Newark - University$62

      Red Roof Inn & Suites Newark - University$62
      Days Inn by Wyndham Newark Wilmington

      Days Inn by Wyndham Newark Wilmington

      900 Churchmans Rd, Newark
        2.0 out of 5.0
         
         

        Situated in the business district, this hotel is 0.9 mi (1.4 km) from Christiana Care Health System and within 6 mi (10 km) of University of Delaware and Christiana ...

        Days Inn by Wyndham Newark Wilmington$64

        Days Inn by Wyndham Newark Wilmington$64
        Red Roof Inn Aberdeen

        Red Roof Inn Aberdeen

        988 Hospitality Way, Aberdeen
          2.0 out of 5.0
           
           

          Situated in a shopping district, this hotel is 1.7 mi (2.8 km) from Ripken Stadium and 1.8 mi (3 km) from Cal Ripken Museum. Aberdeen Proving Ground and Bulle ...

          Red Roof Inn Aberdeen$55

          Red Roof Inn Aberdeen$55
          La Quinta Inn & Suites Newark - Elkton

          La Quinta Inn & Suites Newark - Elkton

          304 Belle Hill Rd, Elkton
            2.5 out of 5.0
             
             

            Situated near the airport, this hotel is 2.9 mi (4.6 km) from Union Hospital and 3 mi (4.9 km) from Historical Society of Cecil County. University of Delaware ...

            La Quinta Inn & Suites Newark - Elkton$89

            La Quinta Inn & Suites Newark - Elkton$89
            Sheraton Wilmington South Hotel

            Sheraton Wilmington South Hotel

            365 Airport Rd, New Castle
              4.0 out of 5.0
               
               

              Situated in the suburbs, this hotel is within 6 mi (10 km) of Banning Park, Christiana Care Health System, and Amstel House. Old Court House and Wilmington and ...

              Sheraton Wilmington South Hotel$101

              Sheraton Wilmington South Hotel$101
              Ramada by Wyndham Newark/Wilmington

              Ramada by Wyndham Newark/Wilmington

              260 Chapman Rd, Newark
                3.0 out of 5.0
                 
                 

                Situated near the airport, this hotel is 2.3 mi (3.7 km) from Christiana Care Health System and 2.6 mi (4.2 km) from Christiana Mall. University of Delaware ...

                Ramada by Wyndham Newark/Wilmington$71

                Ramada by Wyndham Newark/Wilmington$71
                Comfort Inn & Suites Newark - Wilmington

                Comfort Inn & Suites Newark - Wilmington

                3 Concord Ln, Newark
                  2.5 out of 5.0
                   
                   

                  Situated near the airport, this hotel is 1.6 mi (2.6 km) from Christiana Care Health System and 2.9 mi (4.7 km) from Meadowood Shopping Center. University of ...

                  Comfort Inn & Suites Newark - Wilmington$84

                  Comfort Inn & Suites Newark - Wilmington$84
                  Red Roof Inn PLUS+ Wilmington - Newark

                  Red Roof Inn PLUS+ Wilmington - Newark

                  415 Stanton Christiana Road, Newark
                    2.5 out of 5.0
                     
                     

                    Situated near the airport, this motel is 1.9 mi (3.1 km) from Christiana Care Health System and within 6 mi (10 km) of Christiana Mall and Meadowood Shopping ...

                    Red Roof Inn PLUS+ Wilmington - Newark$70

                    Red Roof Inn PLUS+ Wilmington - Newark$70
                    Baymont by Wyndham Newark at University of Delaware

                    Baymont by Wyndham Newark at University of Delaware

                    630 S College Ave, Newark
                      2.5 out of 5.0
                       
                       

                      Located in the heart of Newark, this hotel is 0.2 mi (0.4 km) from Bob Carpenter Center and within 3 mi (5 km) of University of Delaware and Newark Shopping ...

                      Baymont by Wyndham Newark at University of Delaware$64

                      Baymont by Wyndham Newark at University of Delaware$64

                      Top Flight Deals

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