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Jackson Vacations

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

Hotwire can help you find your travel bliss with Jackson 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 Jackson

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 Jackson 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 Jackson well.

Top Hotel Deals

See all 122 Hotels in Jackson
Comfort Inn & Suites Jackson - West Bend

Comfort Inn & Suites Jackson - West Bend

W227 N16890 Tillie Lake Ct, Jackson
    2.5 out of 5.0
     
     

    Situated in Jackson, this hotel is 2.6 mi (4.2 km) from Washington County Fair Grounds and within 6 mi (10 km) of Kettle Moraine Ice Center and Little Switzerland. ...

    Hyatt Regency Milwaukee

    Hyatt Regency Milwaukee

    333 W Kilbourn Ave, Milwaukee
      4.0 out of 5.0
       
       

      This downtown Milwaukee hotel is located in the city’s bustling center, close to the Milwaukee River, one block from Bradly Center and Milwaukee Theatre, and ...

      Hyatt Regency Milwaukee$107

      Hyatt Regency Milwaukee$107
      Astor Hotel

      Astor Hotel

      924 E Juneau Ave, Milwaukee
        3.0 out of 5.0
         
         

        Located in East Town, this hotel is within a 15-minute walk of Cathedral Square and Milwaukee Art Museum. Discovery World and BMO Harris Bradley Center are also ...

        Astor Hotel$89

        Astor Hotel$89
        Ambassador Hotel - Milwaukee

        Ambassador Hotel - Milwaukee

        2308 W Wisconsin Ave, Milwaukee
          4.0 out of 5.0
           
           

          This restored 1920s Art Deco hotel, located in downtown Milwaukee, is 4 blocks from Marquette University, and near many conveniences, such as train and metro ...

          Ambassador Hotel - Milwaukee$82

          Ambassador Hotel - Milwaukee$82
          Embassy Suites by Hilton Milwaukee Brookfield

          Embassy Suites by Hilton Milwaukee Brookfield

          1200 S Moorland Rd, Brookfield
            3.5 out of 5.0
             
             

            This family-friendly Brookfield hotel is located in the business district, within 3 mi (5 km) of Brookfield Square Mall and New Berlin Hills Golf Course. Sky ...

            Courtyard by Marriott Milwaukee Brookfield

            Courtyard by Marriott Milwaukee Brookfield

            16865 W Bluemound Rd, Brookfield
              3.0 out of 5.0
               
               

              Situated in the suburbs, this hotel is 1 mi (1.6 km) from Brookfield Square Mall and within 6 mi (10 km) of Monkey Joe's and Sky Safari. Oceans of Fun and New ...

              Country Inn & Suites by Radisson, Port Washington, WI

              Country Inn & Suites by Radisson, Port Washington, WI

              350 E Seven Hills Rd, Port Washington
                2.5 out of 5.0
                 
                 

                Situated in Port Washington, this hotel is 1.4 mi (2.3 km) from Possibility Playground and within 12 mi (20 km) of Harrington Beach State Park and Covered Bridge. ...

                Country Inn & Suites by Radisson, Port Washington, WI$84

                Country Inn & Suites by Radisson, Port Washington, WI$84
                Hampton Inn Milwaukee/Brookfield

                Hampton Inn Milwaukee/Brookfield

                575 N Barker Rd, Brookfield
                  2.5 out of 5.0
                   
                   

                  Situated in the business district, this hotel is 1.2 mi (2 km) from Monkey Joe's and 2.2 mi (3.6 km) from Lasertag Adventure. Sharon Lynne Wilson Center for ...

                  Days Inn and Suites Milwaukee

                  Days Inn and Suites Milwaukee

                  1840 N 6th St, Milwaukee
                    3.0 out of 5.0
                     
                     

                    Situated in Milwaukee, this hotel is within 1 mi (2 km) of Milwaukee Youth Arts Center and BMO Harris Bradley Center. Milwaukee Art Museum and Charles Allis ...

                    Days Inn and Suites Milwaukee$64

                    Days Inn and Suites Milwaukee$64
                    Radisson Hotel Milwaukee NW (Menomonee Falls)

                    Radisson Hotel Milwaukee NW (Menomonee Falls)

                    N88 W14750 Main St, Menomonee Falls
                      3.0 out of 5.0
                       
                       

                      Situated in Menomonee Falls, this hotel is 0.9 mi (1.5 km) from Harley Davidson Factory and within 9 mi (15 km) of Ray's MTB Indoor Mountain Bike Park and Walter ...