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Healdsburg Vacations

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

Hotwire can help you find your travel bliss with Healdsburg 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 Healdsburg

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 Healdsburg 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 Healdsburg well.

Healdsburg Flight + Hotel packages

Top Hotel Deals

See all 424 Hotels in Healdsburg
Best Western Dry Creek Inn

Best Western Dry Creek Inn

198 Dry Creek Rd, Healdsburg
    3.0 out of 5.0
     
     

    This Healdsburg hotel is within 10 miles of over 200 wineries, the River Rock Casino, and Lake Sonoma.

    Best Western Dry Creek Inn$102

    Best Western Dry Creek Inn$102
    Travelodge by Wyndham Healdsburg - Sonoma Wine Country

    Travelodge by Wyndham Healdsburg - Sonoma Wine Country

    178 Dry Creek Rd, Healdsburg
      2.0 out of 5.0
       
       

      Situated in Healdsburg, this motel is within 1 mi (2 km) of Simi Winery and Raven Performing Arts Theater. Healdsburg Plaza and Healdsburg Center for the Arts ...

      Travelodge by Wyndham Healdsburg - Sonoma Wine Country$110

      Travelodge by Wyndham Healdsburg - Sonoma Wine Country$110
      Calderwood Inn

      Calderwood Inn

      25 West Grant Street, Healdsburg
        3.5 out of 5.0
         
         

        Situated in Healdsburg, this romantic guesthouse is within a 15-minute walk of Raven Performing Arts Theater, Healdsburg Plaza, and Healdsburg Center for the ...

        Americas Best Value Inn and Suites - Healdsburg

        Americas Best Value Inn and Suites - Healdsburg

        74 Healdsburg Ave, Healdsburg
          2.0 out of 5.0
           
           

          Situated in Healdsburg, this motel is within a 15-minute walk of Healdsburg Plaza, Pezzi King Winery, and Healdsburg Center for the Arts. Raven Performing Arts ...

          Americas Best Value Inn and Suites - Healdsburg$87

          Americas Best Value Inn and Suites - Healdsburg$87
          Grape Leaf Inn

          Grape Leaf Inn

          539 Johnson Street, Healdsburg
            4.0 out of 5.0
             
             

            Situated in Healdsburg, this romantic bed & breakfast is within a 10-minute walk of Raven Performing Arts Theater, Healdsburg Center for the Arts, and Healdsburg ...

            Healdsburg Inn on the Plaza, A Four Sisters Inn

            Healdsburg Inn on the Plaza, A Four Sisters Inn

            112 Matheson, Healdsburg
              3.5 out of 5.0
               
               

              Located in the heart of Healdsburg, this romantic bed & breakfast is steps from Healdsburg Plaza, Healdsburg Center for the Arts, and Raven Performing Arts Theater. ...

              Hotel Healdsburg

              Hotel Healdsburg

              25 Matheson St, Healdsburg
                4.0 out of 5.0
                 
                 

                Located in the heart of Healdsburg, this spa hotel is within a 5-minute walk of Healdsburg Plaza, Healdsburg Center for the Arts, and Raven Performing Arts Theater. ...

                Hotel Healdsburg$449

                Hotel Healdsburg$449
                h2hotel

                h2hotel

                219 Healdsburg Ave, Healdsburg
                  3.5 out of 5.0
                   
                   

                  Located in the heart of Healdsburg, this hotel is within a 5-minute walk of Healdsburg Plaza, Healdsburg Center for the Arts, and Raven Performing Arts Theater. ...

                  h2hotel$279

                  h2hotel$279
                  Haydon Street Inn

                  Haydon Street Inn

                  321 Haydon Street, Healdsburg
                    3.0 out of 5.0
                     
                     

                    Situated in Healdsburg, this bed & breakfast is within a 10-minute walk of Healdsburg Museum and Healdsburg Plaza. Healdsburg Ridge Open Space Preserve and Dry ...

                    Duchamp Hotel Private Suites

                    Duchamp Hotel Private Suites

                    421 Foss St, Healdsburg
                      3.5 out of 5.0
                       
                       

                      Situated in the city center, this hotel is close to Raven Performing Arts Theater, Healdsburg Plaza, and Healdsburg Center for the Arts. Also nearby are Healdsburg ...

                      Duchamp Hotel Private Suites$337

                      Duchamp Hotel Private Suites$337

                      Top Flight Deals

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