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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 174 Properties in Sheboygan
Baymont by Wyndham Manitowoc Lakefront

Baymont by Wyndham 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 ...

    Baymont by Wyndham Manitowoc Lakefront$99

    Baymont by Wyndham Manitowoc Lakefront$99
    La Quinta Inn Sheboygan

    La Quinta Inn Sheboygan

    2932 Kohler Memorial Dr, Sheboygan
      2.5 out of 5.0
       
       

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

      La Quinta Inn Sheboygan$84

      La Quinta Inn Sheboygan$84
      The Osthoff Resort

      The Osthoff Resort

      101 Osthoff Avenue, Elkhart Lake
        3.5 out of 5.0
         
         

        Situated in Elkhart Lake, this spa resort is 2.8 mi (4.4 km) from Kettle Moraine State Forest and 2.9 mi (4.7 km) from Road America. Antoinette and Sheboygan ...

        The Osthoff Resort$265

        The Osthoff Resort$265
        Baymont by Wyndham Plymouth

        Baymont by Wyndham Plymouth

        678 Walton Drive, Plymouth
          2.5 out of 5.0
           
           

          Situated in Plymouth, this hotel is within 3 mi (5 km) of Evergreen Golf Course, Sheboygan County Fairgrounds, and Antoinette. Kettle Moraine State Forest and ...

          Baymont by Wyndham Plymouth$106

          Baymont by Wyndham Plymouth$106
          AmericInn by Wyndham Manitowoc

          AmericInn by Wyndham Manitowoc

          5020 Hecker Rd, Manitowoc
            2.5 out of 5.0
             
             

            This family-friendly hotel is in the center of Manitowoc, within 6 mi (10 km) of Wisconsin Maritime Museum, Lincoln Park Zoo, and Rahr West Art Museum. West ...

            AmericInn by Wyndham Manitowoc$102

            AmericInn by Wyndham Manitowoc$102
            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 ...

              Harbor Winds Hotel Sheboygan$89

              Harbor Winds Hotel Sheboygan$89
              AmericInn by Wyndham Sheboygan

              AmericInn by Wyndham Sheboygan

              3664 S Taylor Dr, Sheboygan
                2.0 out of 5.0
                 
                 

                Situated in a shopping district, this hotel is 2.1 mi (3.4 km) from University of Wisconsin-Sheboygan and 2.9 mi (4.6 km) from Sheboygan County Historical Museum. ...

                AmericInn by Wyndham Sheboygan$109

                AmericInn by Wyndham Sheboygan$109
                Super 8 by Wyndham Sheboygan WI

                Super 8 by Wyndham 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. University of Wisconsin-Sheboygan ...

                  Super 8 by Wyndham Sheboygan WI$74

                  Super 8 by Wyndham Sheboygan WI$74
                  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 ...

                    Grandstay Residential Suites Hotel - Sheboygan$120

                    Grandstay Residential Suites Hotel - Sheboygan$120
                    Sleep Inn & Suites Sheboygan

                    Sleep Inn & Suites Sheboygan

                    3912 Motel Rd, Sheboygan
                      2.5 out of 5.0
                       
                       

                      Located in a state park, this family-friendly hotel is within 9 mi (15 km) of University of Wisconsin-Sheboygan, Old Plank Road Trail Head, and The Bull at Pinehurst ...

                      Sleep Inn & Suites Sheboygan$95

                      Sleep Inn & Suites Sheboygan$95

                      Top Flight Deals

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