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

Oconomowoc Vacations

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

Hotwire can help you find your travel bliss with Oconomowoc 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 Oconomowoc

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 Oconomowoc 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 Oconomowoc well.

Top Hotel Deals

See all 80 Hotels in Oconomowoc
Hilton Garden Inn Oconomowoc

Hilton Garden Inn Oconomowoc

1443 Pabst Farms Cir, Oconomowoc
    3.0 out of 5.0
     
     

    Situated near the airport, this hotel is 2.9 mi (4.6 km) from Oconomowoc Arts Center and within 6 mi (10 km) of Hawks Inn and Imagination Station. Oconomowoc ...

    Hilton Garden Inn Oconomowoc$90

    Hilton Garden Inn Oconomowoc$90
    Staybridge Suites Milwaukee West-Oconomowoc

    Staybridge Suites Milwaukee West-Oconomowoc

    1141 Blue Ribbon Drive, Oconomowoc
      3.0 out of 5.0
       
       

      Situated in Oconomowoc, this hotel is within 6 mi (10 km) of Oconomowoc Arts Center, Imagination Station, and Oconomowoc Historical Museum. Theatre On Main and ...

      Staybridge Suites Milwaukee West-Oconomowoc$104

      Staybridge Suites Milwaukee West-Oconomowoc$104
      Inn at Pine Terrace

      Inn at Pine Terrace

      351 East Lisbon Road, Oconomowoc
        3.0 out of 5.0
         
         

        Situated in Oconomowoc, this bed & breakfast is within a 15-minute walk of Lac La Belle and Fowler Lake Park. Oconomowoc Historical Museum and Oconomowoc Arts ...

        Inn at Pine Terrace$154

        Inn at Pine Terrace$154
        Quality Inn

        Quality Inn

        5442 North Lovers Ln Rd, Milwaukee
          2.5 out of 5.0
           
           

          Located in the heart of Milwaukee, this hotel is 2.4 mi (3.9 km) from Annunciation Greek Orthodox Church and within 6 mi (10 km) of Mayfair Mall and Harley Davidson ...

          Quality Inn$55

          Quality Inn$55
          Hyatt Place Milwaukee West

          Hyatt Place Milwaukee West

          11777 W Silver Spring Drive, Milwaukee
            3.0 out of 5.0
             
             

            Situated in the suburbs, this hotel is 2.7 mi (4.4 km) from Annunciation Greek Orthodox Church and within 6 mi (10 km) of Mayfair Mall and Harley Davidson Factory. ...

            Hyatt Place Milwaukee West$88

            Hyatt Place Milwaukee West$88
            Wildwood Lodge

            Wildwood Lodge

            N14 W24121 Tower Place, Pewaukee
              2.5 out of 5.0
               
               

              Situated in Pewaukee, this hotel is within 16 mi (25 km) of Wisconsin State Fair Park, Miller Park, and Miller Brewery. Harley-Davidson Museum and Henry W. Maier ...

              Wildwood Lodge$101

              Wildwood Lodge$101
              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 (3.5 km) from Lasertag Adventure. Sharon Lynne Wilson Center for ...

                Hampton Inn Milwaukee/Brookfield$101

                Hampton Inn Milwaukee/Brookfield$101
                DoubleTree by Hilton Milwaukee - Brookfield

                DoubleTree by Hilton Milwaukee - Brookfield

                18155 W Bluemound Rd, Brookfield
                  3.5 out of 5.0
                   
                   

                  Situated in Brookfield, this hotel is 1.8 mi (3 km) from Brookfield Square Mall and 2.6 mi (4.1 km) from Monkey Joe's. Lasertag Adventure and Sharon Lynne Wilson ...

                  DoubleTree by Hilton Milwaukee - Brookfield$108

                  DoubleTree by Hilton Milwaukee - Brookfield$108
                  Sheraton Milwaukee Brookfield Hotel

                  Sheraton Milwaukee Brookfield Hotel

                  375 S Moorland Rd, Brookfield
                    3.5 out of 5.0
                     
                     

                    Renovated February 2014, Sheraton Milwaukee Brookfield sits off I-94 at the Moorland Road Exit, within 11 miles of downtown Milwaukee, the zoo, Miller Park, ...

                    Best Western Premier Milwaukee-Brookfield Hotel & Suites

                    Best Western Premier Milwaukee-Brookfield Hotel & Suites

                    1005 S Moorland Rd, Brookfield
                      3.0 out of 5.0
                       
                       

                      Situated in Brookfield, this hotel is 0.8 mi (1.3 km) from Brookfield Square Mall and 2.5 mi (4.1 km) from New Berlin Hills Golf Course. Oceans of Fun and Milwaukee ...

                      Best Western Premier Milwaukee-Brookfield Hotel & Suites$84

                      Best Western Premier Milwaukee-Brookfield Hotel & Suites$84

                      Top Flight Deals

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