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Gregory Vacations

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

Hotwire can help you find your travel bliss with Gregory 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 Gregory

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 Gregory 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 Gregory well.

Top Hotel Deals

See all 16 Hotels in Gregory
Howard Johnson Hotel & Suites by Wyndham Oacoma

Howard Johnson Hotel & Suites by Wyndham Oacoma

203 E Hwy 16, Oacoma
    2.0 out of 5.0
     
     

    Situated in a rural location, this hotel is within 6 mi (10 km) of Cozard Memorial Library, South Dakota Hall Fame, and Chamberlain Marina. Akta Lakota Museum ...

    Howard Johnson Hotel & Suites by Wyndham Oacoma$76

    Howard Johnson Hotel & Suites by Wyndham Oacoma$76
    AmericInn by Wyndham Chamberlain - Conference Center

    AmericInn by Wyndham Chamberlain - Conference Center

    1981 East King Street, Chamberlain
      2.5 out of 5.0
       
       

      Located in the heart of Chamberlain, this hotel is 3 mi (4.9 km) from Cozard Memorial Library and within 6 mi (10 km) of Lewis and Clark Interpretive and Keelboat ...

      AmericInn by Wyndham Chamberlain - Conference Center$127

      AmericInn by Wyndham Chamberlain - Conference Center$127
      Best Western Lee's Motor Inn

      Best Western Lee's Motor Inn

      220 W King Avenue, Chamberlain
        2.5 out of 5.0
         
         

        Situated in Chamberlain, this motel is within a 15-minute walk of Cozard Memorial Library and Chamberlain Marina. South Dakota Hall Fame and Akta Lakota Museum ...

        Best Western Lee's Motor Inn$85

        Best Western Lee's Motor Inn$85
        Super 8 by Wyndham Chamberlain SD

        Super 8 by Wyndham Chamberlain SD

        Box 36 Lakeview Heights, Chamberlain
          2.0 out of 5.0
           
           

          Situated in Chamberlain, this motel is within a 15-minute walk of Cozard Memorial Library and Chamberlain Marina. South Dakota Hall Fame and Akta Lakota Museum ...

          Super 8 by Wyndham Chamberlain SD$68

          Super 8 by Wyndham Chamberlain SD$68
          Baymont by Wyndham Oacoma

          Baymont by Wyndham Oacoma

          1100 E Hwy 16, Oacoma
            2.0 out of 5.0
             
             

            Situated on a river, this hotel is within 6 mi (10 km) of Cozard Memorial Library, Chamberlain Marina, and South Dakota Hall Fame. Akta Lakota Museum And Cultural ...

            Baymont by Wyndham Oacoma$115

            Baymont by Wyndham Oacoma$115
            Budget Host Inn Gerrys Motel

            Budget Host Inn Gerrys Motel

            203 W SD Hwy 248, Kennebec
              2.5 out of 5.0
               
               

              Situated in Kennebec, this motel is 1 mi (1.6 km) from St. Michael's Catholic Church.

              Arrowwood Resort at Cedar Shore

              Arrowwood Resort at Cedar Shore

              1500 Shoreline Drive, Oacoma
                3.0 out of 5.0
                 
                 

                Set in Oacoma, this family-friendly hotel is within 6 mi (10 km) of Cozard Memorial Library, South Dakota Hall Fame, and Akta Lakota Museum And Cultural Center. ...

                Arrowwood Resort at Cedar Shore$110

                Arrowwood Resort at Cedar Shore$110
                Knights Inn Winner

                Knights Inn Winner

                845 E. Highway 44, Winner
                  1.5 out of 5.0
                   
                   

                  Located in the heart of Winner, this motel is within 1 mi (2 km) of Tripp County Veteran’s Memorial, Winner City Pool, and Winner Country Club.

                  Knights Inn Winner$58

                  Knights Inn Winner$58
                  Quality Inn Oacoma

                  Quality Inn Oacoma

                  100 W Hwy 16, Oacoma
                     
                     

                    Located in the heart of Oacoma, this hotel is within 6 mi (10 km) of South Dakota Hall Fame, Cozard Memorial Library, and Chamberlain Marina. Lewis and Clark ...

                    Super 8 by Wyndham Winner SD

                    Super 8 by Wyndham Winner SD

                    902 E Highway 44, Winner
                      2.0 out of 5.0
                       
                       

                      Situated in a rural location, this motel is within 1 mi (2 km) of Tripp County Veteran’s Memorial, Winner City Pool, and Winner Country Club.

                      Super 8 by Wyndham Winner SD$65

                      Super 8 by Wyndham Winner SD$65