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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 79 Hotels in Middletown
Wayside Inn

Wayside Inn

7783 Main St, Middletown
    3.5 out of 5.0
     
     

    Situated in Middletown, this inn is within 1 mi (2 km) of Wayside Theater and Cedar Creek and Belle Grove National Historical Park. Cedar Creek Battlefield Foundation ...

    Wayside Inn$95

    Wayside Inn$95
    Econo Lodge Inn & Suites

    Econo Lodge Inn & Suites

    91 Reliance Road, Middletown
      2.0 out of 5.0
       
       

      Located in the heart of Middletown, this hotel is 0.7 mi (1.1 km) from Wayside Theater and within 3 mi (5 km) of Cedar Creek and Belle Grove National Historical ...

      Econo Lodge Inn & Suites$74

      Econo Lodge Inn & Suites$74
      La Quinta Inn & Suites Winchester

      La Quinta Inn & Suites Winchester

      1055 Millwood Pike, Route 50 East, Winchester
        3.0 out of 5.0
         
         

        Situated in the suburbs, this hotel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom ...

        La Quinta Inn & Suites Winchester$99

        La Quinta Inn & Suites Winchester$99
        Comfort Inn Woodstock Shenandoah

        Comfort Inn Woodstock Shenandoah

        1011 Motel Dr, Woodstock
          2.5 out of 5.0
           
           

          Located in the heart of Woodstock, this hotel is within 1 mi (2 km) of Shenandoah County Fairgrounds and W.O. Riley Park. Woodstock Museum and 7 East Gallery ...

          Comfort Inn Woodstock Shenandoah$92

          Comfort Inn Woodstock Shenandoah$92
          Comfort Inn Winchester

          Comfort Inn Winchester

          1601 Martinsburg Pike, Winchester
            2.5 out of 5.0
             
             

            Set in Winchester, this family-friendly hotel is within 6 mi (10 km) of Stonewall Jackson's Headquarters, Apple Blossom Mall, and Jim Barnett Park. Bright Box ...

            Comfort Inn Winchester$99

            Comfort Inn Winchester$99
            Country Inn & Suites by Radisson, Winchester, VA

            Country Inn & Suites by Radisson, Winchester, VA

            141 Kernstown Commons Blvd, Winchester
              3.0 out of 5.0
               
               

              Situated in Winchester, this hotel is within 6 mi (10 km) of The Kernstown Battlefield, Shenandoah University, and Rock Harbor Golf Course. Shenandoah Valley ...

              Country Inn & Suites by Radisson, Winchester, VA$71

              Country Inn & Suites by Radisson, Winchester, VA$71
              Red Roof Inn Winchester, VA

              Red Roof Inn Winchester, VA

              991 Millwood Pike, Winchester
                2.0 out of 5.0
                 
                 

                Located in the heart of Winchester, this hotel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and ...

                Red Roof Inn Winchester, VA$65

                Red Roof Inn Winchester, VA$65
                Travelodge by Wyndham Winchester

                Travelodge by Wyndham Winchester

                160 Front Royal Pike, Winchester
                  2.0 out of 5.0
                   
                   

                  Situated in Winchester, this motel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom ...

                  Travelodge by Wyndham Winchester$57

                  Travelodge by Wyndham Winchester$57
                  Wingate by Wyndham Winchester

                  Wingate by Wyndham Winchester

                  150 Wingate Dr, Winchester
                    2.5 out of 5.0
                     
                     

                    Situated in Winchester, this hotel is within a 10-minute walk of Abram's Delight, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom ...

                    Wingate by Wyndham Winchester$93

                    Wingate by Wyndham Winchester$93
                    Hampton Inn & Suites Woodstock

                    Hampton Inn & Suites Woodstock

                    1150 Motel Dr, Woodstock
                      2.5 out of 5.0
                       
                       

                      Situated in Woodstock, this hotel is within 1 mi (2 km) of Shenandoah County Fairgrounds and W.O. Riley Park. Woodstock Museum and 7 East Gallery are also within ...

                      Hampton Inn & Suites Woodstock$97

                      Hampton Inn & Suites Woodstock$97

                      Top Flight Deals

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