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Greenport Vacations

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

Hotwire can help you find your travel bliss with Greenport 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 Greenport

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 Greenport 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 Greenport well.

Greenport Flight + Hotel packages

Top Hotel Deals

See all 238 Hotels in Greenport
The Gallery Hotel

The Gallery Hotel

439 Main Street, Greenport
    3.5 out of 5.0
     
     

    Situated in Greenport, this boutique hotel is within a 10-minute walk of Camera Obscura and East End Seaport Maritime Museum. Railroad Museum of Long Island ...

    American Beech Hotel

    American Beech Hotel

    300 Main Street, Greenport
      3.5 out of 5.0
       
       

      Situated by the sea, this inn is within a 10-minute walk of Camera Obscura and East End Seaport Maritime Museum. Railroad Museum of Long Island and Kontokosta ...

      Cliffside Resort Condominiums

      Cliffside Resort Condominiums

      61475 Route 48 (North Road), Greenport
        3.0 out of 5.0
         
         

        Offering direct access to the beach, this Greenport condo building is within 3 mi (5 km) of Kontokosta Winery, 67 Steps Beach, and Norman E. Klipp Marine Park. ...

        Sound View Greenport

        Sound View Greenport

        58775 Route 48, Greenport
          3.0 out of 5.0
           
           

          Nestled on the beach, this Greenport hotel is within 3 mi (5 km) of Kontokosta Winery, 67 Steps Beach, and Norman E. Klipp Marine Park. Island's End Golf and ...

          Fordham House

          Fordham House

          817 Main Street, Greenport
            3.0 out of 5.0
             
             

            Situated in Greenport, this bed & breakfast is within a 15-minute walk of Kontokosta Winery and Camera Obscura. 67 Steps Beach and East End Seaport Maritime ...

            Harbor Knoll Bed & Breakfast

            Harbor Knoll Bed & Breakfast

            424 4th Street, Greenport
              3.0 out of 5.0
               
               

              Situated in Greenport, this beach bed & breakfast is steps from Railroad Museum of Long Island and East End Seaport Maritime Museum.

              Stirling House Bed & Breakfast

              Stirling House Bed & Breakfast

              104 Bay Avenue, Greenport
                3.0 out of 5.0
                 
                 

                Situated on the waterfront, this bed & breakfast is within a 15-minute walk of East End Seaport Maritime Museum and Railroad Museum of Long Island. Kontokosta ...

                The Atlantic Hotel

                The Atlantic Hotel

                1655 County Road 39, Southampton
                  2.5 out of 5.0
                   
                   

                  Situated by the ocean, this hotel is 1 mi (1.7 km) from Shinnecock Hills Golf Course and within 3 mi (5 km) of Shinnecock Nation Cultural Center and Museum and ...

                  The Atlantic Hotel$189

                  The Atlantic Hotel$189
                  Water's Edge Resort & Spa

                  Water's Edge Resort & Spa

                  1525 Boston Post Road, Westbrook
                    3.5 out of 5.0
                     
                     

                    This Westbrook resort is on the beach, 1.7 mi (2.8 km) from Tanger Outlets, and within 6 mi (10 km) of Harvey's Beach and Indian River Marina. General William ...

                    Water's Edge Resort & Spa $235

                    Water's Edge Resort & Spa $235
                    Hampton Maid Motel

                    Hampton Maid Motel

                    259 E Montauk Hwy, Southampton
                      2.5 out of 5.0
                       
                       

                      Situated near the beach in Hampton Bays, this motel is close to Meschutt Beach, Shinnecock Hills Golf Course and Shinnecock East County Park. Area attractions ...

                      Top Flight Deals

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