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Ossining Vacations

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

Hotwire can help you find your travel bliss with Ossining 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 Ossining

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 Ossining 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 Ossining well.

Top Hotel Deals

See all 174 Hotels in Ossining
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd, Yonkers
    3.5 out of 5.0
     
     

    Situated in the business district, this hotel is 1.5 mi (2.5 km) from Legoland Discovery Center Westchester and 2.6 mi (4.1 km) from Sarah Lawrence College. ...

    Royal Regency Hotel$103

    Royal Regency Hotel$103
    Tarrytown House Estate on the Hudson

    Tarrytown House Estate on the Hudson

    49 E Sunnyside Lane, Tarrytown
      3.5 out of 5.0
       
       

      Situated in the historical district, this hotel is within 1 mi (2 km) of Lyndhurst Mansion and Irvington Town Hall Theater. Memorial Park and Matthiessen Park ...

      Tarrytown House Estate on the Hudson$134

      Tarrytown House Estate on the Hudson$134
      DoubleTree by Hilton Tarrytown

      DoubleTree by Hilton Tarrytown

      455 S Broadway, Tarrytown
        3.5 out of 5.0
         
         

        Situated in the historical district, this spa hotel is within 2 mi (3 km) of Lyndhurst Mansion, Pierson Park, and Irvington Town Hall Theater. Tarrytown Lighthouse ...

        DoubleTree by Hilton Tarrytown$95

        DoubleTree by Hilton Tarrytown$95
        Hyatt Regency Greenwich

        Hyatt Regency Greenwich

        1800 E Putnam Avenue, Old Greenwich
          4.0 out of 5.0
           
           

          This Hyatt Regency hotel, located on the Stamford/Greenwich border, is minutes from both the heart of downtown Stamford and shopping on Greenwich Avenue. New ...

          Hyatt Regency Greenwich$99

          Hyatt Regency Greenwich$99
          Hyatt Place New York/Yonkers

          Hyatt Place New York/Yonkers

          7000 Mall Walk, Yonkers
            3.0 out of 5.0
             
             

            Located in the heart of Yonkers, this hotel is within 1 mi (2 km) of Empire City Casino and Sarah Lawrence College. Yonkers Raceway and Grace Baptist Church ...

            Hyatt Place New York/Yonkers$149

            Hyatt Place New York/Yonkers$149
            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
              The Time Nyack

              The Time Nyack

              400 High Avenue, Nyack
                4.0 out of 5.0
                 
                 

                Situated in Nyack, this hotel is within a 15-minute walk of Elmwood Playhouse and Edward Hopper House Art Center. Memorial Park and Rockland Center for the Arts ...

                The Time Nyack$111

                The Time Nyack$111
                Doral Arrowwood

                Doral Arrowwood

                975 Anderson Hill Rd, Rye Brook
                  4.0 out of 5.0
                   
                   

                  This family-friendly Rye Brook hotel is located near the airport, within 2 mi (3 km) of Donald M Kendall Sculpture Gardens, Neuberger Museum of Art, and Performing ...

                  Doral Arrowwood$138

                  Doral Arrowwood$138
                  La Quinta inn & Suites Armonk Westchester County Airport

                  La Quinta inn & Suites Armonk Westchester County Airport

                  94 Business Park Dr, Armonk
                    2.5 out of 5.0
                     
                     

                    Situated in Armonk, this hotel is 0.5 mi (0.8 km) from Armonk Indoor Sports Center and within 6 mi (10 km) of Audubon Center and Westmoreland Sanctuary. Arthur ...

                    La Quinta inn & Suites Armonk Westchester County Airport$93

                    La Quinta inn & Suites Armonk Westchester County Airport$93
                    Westchester Marriott

                    Westchester Marriott

                    670 White Plains Rd, Tarrytown
                      3.5 out of 5.0
                       
                       

                      Situated in the suburbs, this spa hotel is within 2 mi (3 km) of Greenburgh Public Library, Sportime USA, and Westchester Skating Academy. Captain Lawrence Brewing ...

                      Westchester Marriott$144

                      Westchester Marriott$144

                      Top Flight Deals

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