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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 124 Hotels in New Windsor
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
    Homewood Suites Stewart Airport

    Homewood Suites Stewart Airport

    180 Breunig Rd, New Windsor
      3.0 out of 5.0
       
       

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

      Homewood Suites Stewart Airport$118

      Homewood Suites Stewart Airport$118
      Windsor Motel

      Windsor Motel

      2976 US Route 9W, New Windsor
        2.0 out of 5.0
         
         

        Situated in New Windsor, this hotel is within 3 mi (5 km) of Knox's Headquarters State Historic Site, Washington Headquarters, and Motorcyclepedia Museum. Delano-Hitch ...

        Econo Lodge Near Stewart Inter

        Econo Lodge Near Stewart Inter

        310 Windsor Hwy, New Windsor
          2.0 out of 5.0
           
           

          Situated near the airport, this hotel is 0.8 mi (1.3 km) from Knox's Headquarters State Historic Site and within 3 mi (5 km) of National Purple Heart Hall of ...

          Econo Lodge Near Stewart Inter$80

          Econo Lodge Near Stewart Inter$80
          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
            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
              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 within 3 mi (5 km) of Galleria at Crystal Run, Orange County Fair Speedway, and Orange County Fairgrounds. ...

                Microtel Inn & Suites by Wyndham Middletown$84

                Microtel Inn & Suites by Wyndham Middletown$84
                Ramada by Wyndham Fishkill

                Ramada by Wyndham Fishkill

                542 Route 9, Fishkill
                  3.0 out of 5.0
                   
                   

                  Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum, Fishkill Golf Course, and Blodgett Memorial Library. SplashDown Beach is ...

                  Ramada by Wyndham Fishkill$99

                  Ramada by Wyndham Fishkill$99
                  Hampton Inn & Suites Poughkeepsie

                  Hampton Inn & Suites Poughkeepsie

                  2361 South Rd, Crown Heights
                    2.5 out of 5.0
                     
                     

                    Situated in the historical district, this hotel is 0.2 mi (0.3 km) from Casperkill Golf Club and within 3 mi (5 km) of Locust Grove and McCann Golf Course. Poughkeepsie ...

                    Hampton Inn & Suites Poughkeepsie$114

                    Hampton Inn & Suites Poughkeepsie$114
                    Magnuson Hotel Fishkill

                    Magnuson Hotel Fishkill

                    20 Schuyler Blvd, Fishkill
                      2.5 out of 5.0
                       
                       

                      Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum, Blodgett Memorial Library, and Fishkill Golf Course. SplashDown Beach is ...

                      Magnuson Hotel Fishkill$95

                      Magnuson Hotel Fishkill$95

                      Top Flight Deals

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