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

Winchester Bay Vacations

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

Hotwire can help you find your travel bliss with Winchester Bay 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 Winchester Bay

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 Winchester Bay 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 Winchester Bay well.

Top Hotel Deals

See all 63 Properties in Winchester Bay
Winchester Bay Inn

Winchester Bay Inn

390 Broadway Ave, Winchester Bay
    2.5 out of 5.0
     
     

    Situated near the beach, this motel is 0.1 mi (0.2 km) from Oregon Dunes National Recreation Area and 2.1 mi (3.3 km) from Umpqua Lighthouse. Umpqua Discovery ...

    Winchester Bay Inn$89

    Winchester Bay Inn$89
    Best Western Salbasgeon Inn & Suites Of Reedsport

    Best Western Salbasgeon Inn & Suites Of Reedsport

    1400 Highway 101, Reedsport
      2.5 out of 5.0
       
       

      Situated in Reedsport, this hotel is 1 mi (1.6 km) from Umpqua Discovery Center and 2.6 mi (4.1 km) from Oregon Dunes National Recreation Area. Umpqua Lighthouse ...

      Best Western Salbasgeon Inn & Suites Of Reedsport$114

      Best Western Salbasgeon Inn & Suites Of Reedsport$114
      Quality Inn & Suites at Coos Bay

      Quality Inn & Suites at Coos Bay

      1503 Virginia Ave, North Bend
        2.5 out of 5.0
         
         

        Situated near the beach, this hotel is 0.1 mi (0.2 km) from Pony Village Mall and within 6 mi (10 km) of Coos Bay Boardwalk and Oregon Dunes National Recreation ...

        Quality Inn & Suites at Coos Bay$104

        Quality Inn & Suites at Coos Bay$104
        The Mill Casino Hotel And Rv Park

        The Mill Casino Hotel And Rv Park

        3201 TREMONT AVE,, NORTH BEND
          2.0 out of 5.0
           
           

          Situated in North Bend, this golf campground is 1.6 mi (2.5 km) from Pony Village Mall and 2.1 mi (3.4 km) from Coos Bay Boardwalk. Oregon Dunes National Recreation ...

          Best Western Pier Point Inn

          Best Western Pier Point Inn

          85625 Highway 101, Florence
            2.5 out of 5.0
             
             

            Situated on a river, this hotel is steps from Oregon Dunes National Recreation Area and Suislaw River Bridge. Siuslaw Pioneer Museum and Sandland Adventures ...

            Best Western Pier Point Inn$190

            Best Western Pier Point Inn$190
            Anchor Bay Inn

            Anchor Bay Inn

            1821 Winchester Ave, Reedsport
              2.0 out of 5.0
               
               

              Situated near the beach, this motel is 1.4 mi (2.2 km) from Umpqua Discovery Center and 2.1 mi (3.5 km) from Oregon Dunes National Recreation Area. Umpqua Lighthouse ...

              Anchor Bay Inn$65

              Anchor Bay Inn$65
              Ocean Breeze Motel

              Ocean Breeze Motel

              85165 Hwy 101 South, Florence
                2.0 out of 5.0
                 
                 

                Situated in Florence, this motel is within a 10-minute walk of Oregon Dunes National Recreation Area and Sandland Adventures. Suislaw River Bridge and Jessie ...

                Ocean Breeze Motel$110

                Ocean Breeze Motel$110
                Best Budget Inn

                Best Budget Inn

                1894 Winchester Avenue, Reedsport
                  2.0 out of 5.0
                   
                   

                  Located in the heart of Reedsport, this motel is 1.4 mi (2.2 km) from Umpqua Discovery Center and 2.1 mi (3.4 km) from Oregon Dunes National Recreation Area. ...

                  Best Budget Inn$46

                  Best Budget Inn$46
                  Bay Bridge Motel

                  Bay Bridge Motel

                  66304 Highway 101, North Bend
                    2.0 out of 5.0
                     
                     

                    Situated by the ocean, this motel is 2 mi (3.2 km) from Oregon Dunes National Recreation Area and 2.5 mi (4.1 km) from Pony Village Mall. Coos Bay Boardwalk ...

                    Bay Bridge Motel$65

                    Bay Bridge Motel$65
                    Economy Inn Reedsport

                    Economy Inn Reedsport

                    1593 Highway 101, Reedsport
                      2.0 out of 5.0
                       
                       

                      Situated in Reedsport, this motel is 1.1 mi (1.8 km) from Umpqua Discovery Center and 2.4 mi (3.9 km) from Oregon Dunes National Recreation Area. Umpqua Lighthouse ...

                      Economy Inn Reedsport$70

                      Economy Inn Reedsport$70

                      Top Flight Deals

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