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New Windsor Vacations

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

Hotwire can help you find your travel bliss with New 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 New 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 New 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 New Windsor well.

Top Hotel Deals

See all 98 Hotels in New Windsor
Days Inn by Wyndham Gettysburg

Days Inn by Wyndham Gettysburg

865 York Rd, Gettysburg
    2.5 out of 5.0
     
     

    Situated in Gettysburg, this hotel is within 1 mi (2 km) of The David Wills House, Majestic Theater, and Gettysburg Convention & Visitors Bureau. Gettysburg ...

    Days Inn by Wyndham Gettysburg$76

    Days Inn by Wyndham Gettysburg$76
    Eisenhower Hotel & Conference Center

    Eisenhower Hotel & Conference Center

    2634 Emmitsburg Road, Gettysburg
      3.0 out of 5.0
       
       

      Situated in Gettysburg, this hotel is 0.3 mi (0.5 km) from Gettysburg Allstar Expo Complex and 2.4 mi (3.9 km) from Eisenhower National Historic Site. Little ...

      Eisenhower Hotel & Conference Center$62

      Eisenhower Hotel & Conference Center$62
      Aspire Gettysburg Hotel

      Aspire Gettysburg Hotel

      2634-A Emmitsburg Road, Gettysburg
        3.0 out of 5.0
         
         

        Situated in Gettysburg, this hotel is 0.3 mi (0.5 km) from Gettysburg Allstar Expo Complex and 2.5 mi (4 km) from Eisenhower National Historic Site. Little Round ...

        Aspire Gettysburg Hotel$71

        Aspire Gettysburg Hotel$71
        Hyatt Place Baltimore/Owings Mills

        Hyatt Place Baltimore/Owings Mills

        4730 Painters Mill Rd, Owings Mills
          3.0 out of 5.0
           
           

          Situated in the business district, this hotel is within 9 mi (15 km) of Stevenson University, Diamond Ridge Golf Course, and Jewish Community Center of Baltimore. ...

          Hyatt Place Baltimore/Owings Mills$100

          Hyatt Place Baltimore/Owings Mills$100
          Country Inn & Suites by Radisson, Gettysburg, PA

          Country Inn & Suites by Radisson, Gettysburg, PA

          1857 Gettysburg Village Dr, Gettysburg
            3.0 out of 5.0
             
             

            Situated in a national park, this hotel is within 2 mi (3 km) of Outlet Shoppes at Gettysburg, Mulligan MacDuffer Adventure Golf, and Gettysburg National Military ...

            Country Inn & Suites by Radisson, Gettysburg, PA$88

            Country Inn & Suites by Radisson, Gettysburg, PA$88
            Days Inn by Wyndham Frederick

            Days Inn by Wyndham Frederick

            5646 Buckeystown Pike, Frederick
              2.0 out of 5.0
               
               

              Situated in Frederick, this hotel is within 1 mi (2 km) of Francis Scott Key Mall, Westview Promenade, and Harry Grove Stadium. Monocacy National Battlefied ...

              Days Inn by Wyndham Frederick$63

              Days Inn by Wyndham Frederick$63
              Best Western Historic Frederick

              Best Western Historic Frederick

              420 Prospect Blvd, Frederick
                2.5 out of 5.0
                 
                 

                Situated in Frederick, this hotel is within 3 mi (5 km) of National Museum of Civil War Medicine, Harry Grove Stadium, and Frederick Fairgrounds. Francis Scott ...

                Best Western Historic Frederick$77

                Best Western Historic Frederick$77
                Super 8 by Wyndham Frederick

                Super 8 by Wyndham Frederick

                20 Monocacy Blvd, Frederick
                  2.0 out of 5.0
                   
                   

                  Situated in Frederick, this hotel is within 1 mi (2 km) of Harry Grove Stadium and National Museum of Civil War Medicine. Frederick Fairgrounds and Francis Scott ...

                  Super 8 by Wyndham Frederick$51

                  Super 8 by Wyndham Frederick$51
                  The Lodges at Gettysburg

                  The Lodges at Gettysburg

                  685 Camp Gettysburg Road, Gettysburg
                    3.0 out of 5.0
                     
                     

                    Situated on a lake, this cabin is within 6 mi (10 km) of Liberty Mountain Ski Resort, Devil's Den, and Little Round Top. Gettysburg National Cemetery and Jennie ...

                    The Lodges at Gettysburg$119

                    The Lodges at Gettysburg$119
                    Super 8 by Wyndham Gettysburg

                    Super 8 by Wyndham Gettysburg

                    869 York Road, Gettysburg
                      2.5 out of 5.0
                       
                       

                      Situated in a rural location, this hotel is within 1 mi (2 km) of The David Wills House and Majestic Theater. Gettysburg Convention & Visitors Bureau and Gettysburg ...

                      Super 8 by Wyndham Gettysburg$61

                      Super 8 by Wyndham Gettysburg$61

                      Top Flight Deals

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