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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 129 Properties in Middletown
Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown

19 Crystal Run Crossing, Middletown
    2.0 out of 5.0
     
     

    Located in the heart of Middletown, this hotel is 1.6 mi (2.5 km) from Galleria at Crystal Run and 2.7 mi (4.4 km) from Orange County Fair Speedway. Orange County ...

    Microtel Inn & Suites by Wyndham Middletown$92

    Microtel Inn & Suites by Wyndham Middletown$92
    Super 8 by Wyndham Middletown

    Super 8 by Wyndham Middletown

    563 Route 211 E, Middletown
      2.0 out of 5.0
       
       

      Situated in Middletown, this motel is within 3 mi (5 km) of Orange County Fairgrounds, Orange County Fair Speedway, and Paramount Theatre. Soons Orchards and ...

      Super 8 by Wyndham Middletown$73

      Super 8 by Wyndham Middletown$73
      Sleep Inn & Suites Middletown - Goshen

      Sleep Inn & Suites Middletown - Goshen

      3491 Route 6, Middletown
        2.5 out of 5.0
         
         

        Located in the heart of Middletown, this hotel is 1.9 mi (3.1 km) from Paramount Theatre and 1.9 mi (3.1 km) from Soons Orchards. Orange County Fair Speedway ...

        Sleep Inn & Suites Middletown - Goshen$99

        Sleep Inn & Suites Middletown - Goshen$99
        Courtyard by Marriott Middletown

        Courtyard by Marriott Middletown

        24 Crystal Run Xing, Middletown
          3.0 out of 5.0
           
           

          Situated in Middletown, this hotel is within 3 mi (5 km) of Galleria at Crystal Run, Orange County Fair Speedway, and Orange County Fairgrounds. Paramount Theatre ...

          Courtyard by Marriott Middletown$121

          Courtyard by Marriott Middletown$121
          Hampton Inn by Hilton Middletown

          Hampton Inn by Hilton Middletown

          20 Crystal Run Crossing, Middletown
            2.5 out of 5.0
             
             

            Situated in the suburbs, this hotel is within 3 mi (5 km) of Galleria at Crystal Run, Orange County Fair Speedway, and Orange County Fairgrounds. Paramount Theatre ...

            Hampton Inn by Hilton Middletown$118

            Hampton Inn by Hilton Middletown$118
            Home2 Suites by Hilton Middletown

            Home2 Suites by Hilton Middletown

            600 Route 211 East, Middletown
              3.0 out of 5.0
               
               

              Situated in Middletown, this hotel is 1.7 mi (2.7 km) from Orange County Fairgrounds and 2.1 mi (3.4 km) from Orange County Fair Speedway. Paramount Theatre ...

              Home2 Suites by Hilton Middletown$143

              Home2 Suites by Hilton Middletown$143
              Americas Best Value Inn-New Paltz

              Americas Best Value Inn-New Paltz

              7 Terwilliger Ln, New Paltz
                2.0 out of 5.0
                 
                 

                Situated in New Paltz, this motel is within 2 mi (3 km) of State University of New York-New Paltz, G. Steve Jordan Gallery, and Loren Campbell Memorial Field. ...

                Americas Best Value Inn-New Paltz$85

                Americas Best Value Inn-New Paltz$85
                Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport

                Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport

                915 Union Ave, New Windsor
                  2.0 out of 5.0
                   
                   

                  Situated in New Windsor, this hotel is within 3 mi (5 km) of Orange County Choppers, National Purple Heart Hall of Honor, and New Windsor Cantonment State Historic ...

                  Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport$84

                  Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport$84
                  Minerals Hotel

                  Minerals Hotel

                  1 Stonehill Dr, Vernon
                    4.0 out of 5.0
                     
                     

                    Conveniently located near the ski slopes, this Vernon resort is within 1 mi (2 km) of Granite Peak Quad, Mountain Creek Ski Resort, and Mountain Creek Waterpark. ...

                    Minerals Hotel$164

                    Minerals Hotel$164
                    Overlook Lodge at Bear Mountain

                    Overlook Lodge at Bear Mountain

                    55 Hessian Drive, Bear Mountain
                      2.5 out of 5.0
                       
                       

                      Situated in a state park, this historic hotel is 1.7 mi (2.7 km) from Bear Mountain State Park and within 6 mi (10 km) of Manitoga The Russel Wright Design Center ...

                      Overlook Lodge at Bear Mountain$149

                      Overlook Lodge at Bear Mountain$149

                      Top Flight Deals

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