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Ashland Vacations

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

Hotwire can help you find your travel bliss with Ashland 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 Ashland

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 Ashland 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 Ashland well.

Top Hotel Deals

See all 148 Hotels in Ashland
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

2525 Ashland St, Ashland
    3.0 out of 5.0
     
     

    Situated in Ashland, this hotel is within 3 mi (5 km) of Schneider Museum of Art, Southern Oregon University, and ScienceWorks Hands-On Museum. North Mountain ...

    Ashland Hills Hotel & Suites$125

    Ashland Hills Hotel & Suites$125
    Plaza Inn & Suites at Ashland Creek

    Plaza Inn & Suites at Ashland Creek

    98 Central Ave, Ashland
      3.0 out of 5.0
       
       

      The Plaza Inn & Suites at Ashland Creek in Ashland is 1 block from Lithia Park, 2 blocks from the Oregon Shakespeare Festival, and 1 mile from Southern Oregon ...

      Plaza Inn & Suites at Ashland Creek$149

      Plaza Inn & Suites at Ashland Creek$149
      Flagship Inn of Ashland

      Flagship Inn of Ashland

      1193 Siskiyou Blvd, Ashland
        2.5 out of 5.0
         
         

        Situated in Ashland, this hotel is within a 10-minute walk of Southern Oregon University and Schneider Museum of Art. Ashland Library and ScienceWorks Hands-On ...

        Flagship Inn of Ashland$90

        Flagship Inn of Ashland$90
        Ashland Springs Hotel

        Ashland Springs Hotel

        212 E Main St, Ashland
          3.0 out of 5.0
           
           

          Ashland Springs Hotel in downtown Ashland is across the street from the Oregon Cabaret Theater and 1 block from the Oregon Shakespeare Festival. Southern Oregon ...

          Ashland Springs Hotel$137

          Ashland Springs Hotel$137
          Best Western Windsor Inn

          Best Western Windsor Inn

          2520 Ashland St, Ashland
            2.5 out of 5.0
             
             

            Situated in Ashland, this hotel is within 3 mi (5 km) of Schneider Museum of Art, Southern Oregon University, and ScienceWorks Hands-On Museum. North Mountain ...

            Best Western Windsor Inn$89

            Best Western Windsor Inn$89
            The Bard's Inn

            The Bard's Inn

            132 N Main Street, Ashland
              2.5 out of 5.0
               
               

              Situated in Ashland, this hotel is within a 10-minute walk of Allen Elizabethan Theatre, Angus Bowmer Theatre, and Thomas Theatre. Oregon Cabaret Theatre and ...

              The Bard's Inn$185

              The Bard's Inn$185
              Stratford Inn

              Stratford Inn

              555 Siskiyou Blvd, Ashland
                2.5 out of 5.0
                 
                 

                Situated near the airport, this hotel is within a 10-minute walk of Ashland Library and Oregon Cabaret Theatre. Southern Oregon University and North Mountain ...

                Stratford Inn$180

                Stratford Inn$180
                Cedarwood Inn of Ashland

                Cedarwood Inn of Ashland

                1801 Siskiyou Blvd, Ashland
                  2.0 out of 5.0
                   
                   

                  Located near the slopes, this Ashland hotel is within 1 mi (2 km) of Schneider Museum of Art and Southern Oregon University and close to winter sports such as ...

                  Cedarwood Inn of Ashland$80

                  Cedarwood Inn of Ashland$80
                  Callahan's Mountain Lodge

                  Callahan's Mountain Lodge

                  7100 Old Highway 99 South, Ashland
                    3.0 out of 5.0
                     
                     

                    Situated in the mountains, this lodge is within 12 mi (20 km) of Emigrant Lake, Mount Ashland Ski Area, and Schneider Museum of Art. Southern Oregon University ...

                    Comfort Inn & Suites

                    Comfort Inn & Suites

                    434 S. Valley View Rd., Ashland
                      2.5 out of 5.0
                       
                       

                      Situated in Ashland, this hotel is within 3 mi (5 km) of Allen Elizabethan Theatre, Angus Bowmer Theatre, and Thomas Theatre. Oregon Cabaret Theatre and Ashland ...

                      Comfort Inn & Suites$99

                      Comfort Inn & Suites$99

                      Top Flight Deals

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