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Middletown Vacations

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

Hotwire can help you find your travel bliss with Middletown 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 Middletown

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 Middletown 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 Middletown well.

Top Hotel Deals

See all 215 Hotels in Middletown
Backyard Garden Oasis

Backyard Garden Oasis

24019 Hilderbrand Drive, Middletown
    3.0 out of 5.0
     
     

    Situated in the mountains, this romantic bed & breakfast is 2.7 mi (4.3 km) from Beaver Creek Vineyards and within 12 mi (20 km) of Robert Louis Stevenson State ...

    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
      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
        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
          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
            Flamingo Conference Resort & Spa

            Flamingo Conference Resort & Spa

            2777 4th St, Santa Rosa
              3.5 out of 5.0
               
               

              Just off scenic Highway 12 and in the heart of Sonoma wine country, this historical landmark is less than 1 mile from Montgomery Village Shopping and a 15 minute ...

              Flamingo Conference Resort & Spa$179

              Flamingo Conference Resort & Spa$179
              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
                Indian Springs Resort & Spa

                Indian Springs Resort & Spa

                1712 Lincoln Avenue, Calistoga
                  3.5 out of 5.0
                   
                   

                  Situated in Calistoga, this spa hotel is 0.3 mi (0.5 km) from Calistoga Visitors Center and within 3 mi (5 km) of Old Faithful Geyser of California and Sterling ...

                  Hotel Santa Rosa

                  Hotel Santa Rosa

                  2632 Cleveland Ave, Santa Rosa
                    2.0 out of 5.0
                     
                     

                    Located in the heart of Santa Rosa, this hotel is within a 15-minute walk of Empire College, Redwood Empire Ice Arena, and Charles M. Schulz Museum. Santa Rosa ...

                    Hotel Santa Rosa$84

                    Hotel Santa Rosa$84
                    Rancho Caymus Inn

                    Rancho Caymus Inn

                    1140 Rutherford Rd., St. Helena
                      4.5 out of 5.0
                       
                       

                      Situated in Rutherford, this luxury inn is close to Beaulieu Vineyard, Robert Mondavi Winery, and Rubicon Estate. Also nearby are Round Pond Estate and Sullivan ...

                      Rancho Caymus Inn$395

                      Rancho Caymus Inn$395

                      Top Flight Deals

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