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Windsor Vacations

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

Hotwire can help you find your travel bliss with Windsor 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 Windsor

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 Windsor 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 Windsor well.

Windsor Flight + Hotel packages

Top Hotel Deals

See all 388 Hotels in Windsor
Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South, Windsor
    2.5 out of 5.0
     
     

    Surrounded by world-class wineries, Hampton Inn & Suites Windsor is a 10-minute drive from Sonoma County’s epicurean hotspot, Healdsburg. The quaint shops and ...

    Hampton Inn & Suites Windsor - Sonoma Wine Country$127

    Hampton Inn & Suites Windsor - Sonoma Wine Country$127
    Holiday Inn Express® Windsor Sonoma Wine Country

    Holiday Inn Express® Windsor Sonoma Wine Country

    8865 Conde Lane, Windsor
      2.5 out of 5.0
       
       

      Located in the heart of Windsor, this hotel is 1.9 mi (3 km) from Windsor Golf Club and 3.1 mi (5 km) from Pacific Coast Air Museum. Kendall-Jackson Wine Estate ...

      Holiday Inn Express® Windsor Sonoma Wine Country$159

      Holiday Inn Express® Windsor Sonoma Wine Country$159
      Holiday Inn Windsor Wine Country

      Holiday Inn Windsor Wine Country

      8755 Old Redwood Hwy, Windsor
        3.0 out of 5.0
         
         

        Situated in Windsor, this hotel is 2 mi (3.2 km) from Windsor Golf Club and within 6 mi (10 km) of Kendall-Jackson Wine Estate and Gardens and Pacific Coast ...

        Holiday Inn Windsor Wine Country$171

        Holiday Inn Windsor Wine Country$171
        WorldMark Windsor

        WorldMark Windsor

        1251 Shilo Rd, Windsor
          3.0 out of 5.0
           
           

          Offering spacious condominiums with the comforts of home, this Sonoma Wine Country resort is next to the Windsor Golf Club, 8 miles from the charming town of ...

          Armida Vineyards Cottage

          Armida Vineyards Cottage

          11940 Old Redwood Hwy, Windsor
            3.5 out of 5.0
             
             

            Situated in Windsor, this vacation home is within 3 mi (5 km) of Pezzi King Winery, Healdsburg Museum, and Healdsburg Center for the Arts. Healdsburg Plaza is ...

            Good Nite Inn Rohnert Park

            Good Nite Inn Rohnert Park

            5040 Redwood Dr, Rohnert Park
              2.0 out of 5.0
               
               

              Situated in Rohnert Park, this hotel is 0.3 mi (0.5 km) from Scandia Family Fun Center and 2.6 mi (4.1 km) from Spreckels Performing Arts Center. Sonoma State ...

              Good Nite Inn Rohnert Park$61

              Good Nite Inn Rohnert Park$61
              Quality Inn Petaluma - Sonoma

              Quality Inn Petaluma - Sonoma

              5100 Montero Way, Petaluma
                2.5 out of 5.0
                 
                 

                Situated in the business district, this hotel is 0.1 mi (0.1 km) from The 101 Casino and within 3 mi (5 km) of University of Northern California and Petaluma ...

                Quality Inn Petaluma - Sonoma$99

                Quality Inn Petaluma - Sonoma$99
                Best Western Plus Wine Country Inn & Suites

                Best Western Plus Wine Country Inn & Suites

                870 Hopper Ave, Santa Rosa
                  2.5 out of 5.0
                   
                   

                  Located in the heart of Santa Rosa, this hotel is within 2 mi (3 km) of Empire College, Charles M. Schulz Museum, and Redwood Empire Ice Arena. Santa Rosa Junior ...

                  Best Western Plus Wine Country Inn & Suites$140

                  Best Western Plus Wine Country Inn & Suites$140
                  Extended Stay America Santa Rosa - South

                  Extended Stay America Santa Rosa - South

                  2600 Corby Ave, Santa Rosa
                    2.5 out of 5.0
                     
                     

                    Situated in Santa Rosa, this hotel is within 3 mi (5 km) of Luther Burbank Home and Gardens, California Welcome Center, and Sonoma County Fairgrounds. Sonoma ...

                    Extended Stay America Santa Rosa - South$103

                    Extended Stay America Santa Rosa - South$103
                    Motel 6 Santa Rosa North

                    Motel 6 Santa Rosa North

                    3145 Cleveland Ave, Santa Rosa
                      2.0 out of 5.0
                       
                       

                      Situated near the airport, this motel is within 1 mi (2 km) of Empire College, Charles M. Schulz Museum, and Redwood Empire Ice Arena. Santa Rosa Junior College ...

                      Motel 6 Santa Rosa North$70

                      Motel 6 Santa Rosa North$70

                      Top Flight Deals

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