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It's time to fly. What's waiting for you in Ossining?

Perhaps you’re searching cheap flights to Ossining for a much-needed vacation or you simply have to roll in to see the relatives. Either way, we say rock that family reunion. Tell one too many stories at the hotel bar. Traveling for work? Crush it. If you lie back and relax without your cell phone, we won’t tell.

In the end you want to score a great deal and have a fantastic time, right? Flying is a small part of the whole adventure. We get that. Wherever you’re excited to go – or get away from – start this story with Hotwire’s cheap flights to Ossining.

Not sure how to get the best price on plane tickets to Ossining?

We know there are some airline aficionados out there. If you don’t know the industry like the back of your hand, don’t worry. You can make spending less look good with our booking tips.

Search certain days of the week for Ossining flights

For better savings, consider departing on a Wednesday, Thursday or Saturday. Return on a Sunday, Tuesday or Wednesday. International deals are often available when departing Monday through Thursday.

Change up your days for cheaper weekend getaways

Jetting off on Thursday and returning on Sunday is generally less expensive than flying on Friday and returning on Monday.

Stay a Saturday night to play more

Spending the weekend at your destination will generally result in lower airfares. We’re all for that.

Consider alternate airports when searching Ossining flights

Other nearby airports may offer different fares from your current search results. Clicking “Nearby Airports” after your initial search will give a list of the closest options.

See a fare that you like? Pounce!

Coordinate with your travel buddies before searching and you’ll be able to act quickly when it’s time to book. Airline ticket prices often change in minutes. We know you’re combing for the best prices but so is everyone else! If the deal is right, snag it and feel the sweet satisfaction of booking victory.

Fly during the off-peak season

Certain travel destinations have especially high volume during particular seasons. For example, Europe, Hawaii and Alaska are big hits in the summer. Florida, New Orleans and Southern California are the most popular in springtime. Winter is prime for Mexico and the Caribbean, as well as ski and snowboard destinations like the Colorado Rockies. In the autumn, Northern California, the Pacific Northwest and New England draw visitors. Flying during less popular periods can mean extra money in your wallet – yes, please!

Last Minute Hotel Deals in Ossining

See all 225 Properties in Ossining
HYATT house White Plains

HYATT house White Plains

101 Corporate Park Drive, West Harrison
    3.0 out of 5.0
     
     

    HYATT house White Plains is a 5-minute drive from the city center, and 12 minutes from Westchester County Airport. Guests can drive 45 minutes to midtown Manhattan. ...

    HYATT house White Plains$118

    HYATT house White Plains$118
    Sheraton Tarrytown Hotel

    Sheraton Tarrytown Hotel

    600 White Plains Rd, Tarrytown
      3.5 out of 5.0
       
       

      Situated in the historical district, this hotel is within 3 mi (5 km) of Tarrytown Music Hall, Sportime USA, and Westchester Skating Academy. Captain Lawrence ...

      Sheraton Tarrytown Hotel$87

      Sheraton Tarrytown Hotel$87
      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$119

        Hyatt Regency Greenwich$119
        DoubleTree by Hilton Tarrytown

        DoubleTree by Hilton Tarrytown

        455 S Broadway, Tarrytown
          3.5 out of 5.0
           
           

          Situated in the historical district, this hotel is within 12 mi (20 km) of Manhattanville College, Purchase College, and Empire City Casino.

          DoubleTree by Hilton Tarrytown$114

          DoubleTree by Hilton Tarrytown$114