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Winston Vacations

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

Hotwire can help you find your travel bliss with Winston 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 Winston

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 Winston 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 Winston well.

Top Hotel Deals

See all 28 Hotels in Winston
Wildlife Inn

Wildlife Inn

251 N Main St, Winston
    2.5 out of 5.0
     
     

    Situated in Winston, this inn is within 3 mi (5 km) of Wildlife Safari, Abacela Winery, and Spangler Vineyards. Douglas County Museum of History and Natural ...

    Wildlife Inn$88

    Wildlife Inn$88
    Safari Inn

    Safari Inn

    101 NE Main Street, Winston
      2.0 out of 5.0
       
       

      Situated in Winston, this motel is within 3 mi (5 km) of Wildlife Safari, Abacela Winery, and Spangler Vineyards. Douglas County Museum of History and Natural ...

      Motel 6 Sutherlin, OR

      Motel 6 Sutherlin, OR

      1400 Hospitality Way, Sutherlin
        2.0 out of 5.0
         
         

        Situated in the business district, this hotel is 0.7 mi (1.2 km) from Umpqua Golf Resort and 1.6 mi (2.5 km) from Central Park. Oakland City Park and Misty Oaks ...

        Travelodge by Wyndham Roseburg Riverfront

        Travelodge by Wyndham Roseburg Riverfront

        315 W Harvard Ave, Roseburg
          2.0 out of 5.0
           
           

          Situated in Roseburg, this motel is 1.4 mi (2.3 km) from Stewart Park and 1.6 mi (2.6 km) from Douglas County Museum of History and Natural History. Spangler ...

          Travelodge by Wyndham Roseburg Riverfront$70

          Travelodge by Wyndham Roseburg Riverfront$70
          Best Western Plus Hartford Lodge

          Best Western Plus Hartford Lodge

          150 Myrtle St, Sutherlin
            2.5 out of 5.0
             
             

            Located in the heart of Sutherlin, this hotel is 0.7 mi (1.1 km) from Umpqua Golf Resort and 1.5 mi (2.3 km) from Central Park. Oakland City Park and Misty Oaks ...

            Best Western Plus Hartford Lodge$120

            Best Western Plus Hartford Lodge$120
            Comfort Inn

            Comfort Inn

            1539 NW Mullholland Drive, Roseburg
              2.5 out of 5.0
               
               

              Situated near the airport, this hotel is 1.7 mi (2.7 km) from Stewart Park and 3.1 mi (4.9 km) from Douglas County Museum of History and Natural History. Winchester ...

              Comfort Inn$120

              Comfort Inn$120
              Windmill Inn of Roseburg

              Windmill Inn of Roseburg

              1450 Nw Mulholland Dr, Roseburg
                2.5 out of 5.0
                 
                 

                Situated near the airport, this hotel is 1.7 mi (2.7 km) from Stewart Park and 3 mi (4.9 km) from Douglas County Museum of History and Natural History. Winchester ...

                Windmill Inn of Roseburg$134

                Windmill Inn of Roseburg$134
                Days Inn by Wyndham Roseburg

                Days Inn by Wyndham Roseburg

                790 NW Garden Valley Blvd, Roseburg
                  2.5 out of 5.0
                   
                   

                  Located in the heart of Roseburg, this motel is 1.4 mi (2.2 km) from Stewart Park and 2.8 mi (4.6 km) from Douglas County Museum of History and Natural History. ...

                  Days Inn by Wyndham Roseburg$56

                  Days Inn by Wyndham Roseburg$56
                  Sleep Inn & Suites

                  Sleep Inn & Suites

                  2855 NW Edenbower Blvd, Roseburg
                    2.5 out of 5.0
                     
                     

                    Situated near the airport, this hotel is 2.4 mi (3.8 km) from Stewart Park and within 6 mi (10 km) of Douglas County Museum of History and Natural History and ...

                    Sleep Inn & Suites$98

                    Sleep Inn & Suites$98
                    Super 8 by Wyndham Roseburg

                    Super 8 by Wyndham Roseburg

                    3200 Nw Aviation Dr I-5 Exit # 127, Roseburg
                      2.0 out of 5.0
                       
                       

                      Situated near the airport, this hotel is 2.8 mi (4.5 km) from Winchester Dam and 2.9 mi (4.6 km) from Stewart Park. Douglas County Museum of History and Natural ...

                      Super 8 by Wyndham Roseburg$70

                      Super 8 by Wyndham Roseburg$70

                      Top Flight Deals

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