Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Sheboygan Vacations

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

Hotwire can help you find your travel bliss with Sheboygan 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 Sheboygan

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 Sheboygan 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 Sheboygan well.

Top Hotel Deals

See all 172 Hotels in Sheboygan
Blue Harbor Resort and Spa

Blue Harbor Resort and Spa

725 Blue Harbor Drive, Sheboygan
    3.0 out of 5.0
     
     

    Nestled on the beach, this Sheboygan resort is within 1 mi (2 km) of John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts. Sheboygan ...

    AmericInn Lodge and Suites Manitowoc

    AmericInn Lodge and Suites Manitowoc

    5020 Hecker Rd, Manitowoc
      2.5 out of 5.0
       
       

      This family-friendly hotel is in the center of Manitowoc, within 9 mi (15 km) of Wisconsin Maritime Museum, Lincoln Park Zoo, and West of the Lake Gardens. Rahr ...

      AmericInn Hotel & Suites Sheboygan

      AmericInn Hotel & Suites Sheboygan

      3664 S Taylor Dr, Sheboygan
        2.0 out of 5.0
         
         

        Situated in a shopping district, this hotel is 2.2 mi (3.6 km) from University of Wisconsin-Sheboygan and 2.9 mi (4.6 km) from Sheboygan County Historical Museum. ...

        Harbor Winds Hotel Sheboygan

        Harbor Winds Hotel Sheboygan

        905 S 8th St, Sheboygan
          2.0 out of 5.0
           
           

          Situated near the boardwalk, this hotel is within a 15-minute walk of John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts. Sheboygan ...

          Baymont Inn & Suites Manitowoc Lakefront

          Baymont Inn & Suites Manitowoc Lakefront

          101 Maritime Dr, Manitowoc
            2.5 out of 5.0
             
             

            Situated on the waterfront, this hotel is within a 15-minute walk of Wisconsin Maritime Museum and Rahr West Art Museum. Lincoln Park Zoo and West of the Lake ...

            Sleep Inn & Suites Sheboygan

            Sleep Inn & Suites Sheboygan

            3912 Motel Rd, Sheboygan
              2.5 out of 5.0
               
               

              Situated in a state park, this hotel is within 9 mi (15 km) of University of Wisconsin-Sheboygan, The Bull at Pinehurst Farms Golf Course, and John Michael Kohler ...

              Harbor Town Inn

              Harbor Town Inn

              4004 Calumet Ave., Manitowoc
                2.0 out of 5.0
                 
                 

                Situated near the airport, this hotel is 2.6 mi (4.2 km) from Wisconsin Maritime Museum and 2.9 mi (4.7 km) from Rahr West Art Museum. West of the Lake Gardens ...

                Fox Hills Resort

                Fox Hills Resort

                250 W. Church St., Mishicot
                  3.0 out of 5.0
                   
                   

                  Situated near the beach, this resort is 0.1 mi (0.2 km) from Fox Hills Country Club and within 9 mi (15 km) of Bernard Schwartz House and Rogers Street Fishing ...

                  Grandstay Residential Suites Hotel - Sheboygan

                  Grandstay Residential Suites Hotel - Sheboygan

                  708 Niagara Avenue, Sheboygan
                    2.5 out of 5.0
                     
                     

                    Situated in Sheboygan, this aparthotel is within a 5-minute walk of Stefanie H. Weill Center for the Performing Arts and John Michael Kohler Arts Center. Sheboygan ...

                    Super 8 Sheboygan WI

                    Super 8 Sheboygan WI

                    3402 Wilgus Avenue, Sheboygan
                      2.0 out of 5.0
                       
                       

                      Situated in Sheboygan, this motel is within 1 mi (2 km) of Sheboygan County Historical Museum and Old Plank Road Trail Head. Stefanie H. Weill Center for the ...

                      Top Flight Deals

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