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Sheffield Island Vacations

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

Hotwire can help you find your travel bliss with Sheffield Island 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 Sheffield Island

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 Sheffield Island 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 Sheffield Island well.

Sheffield Island Flight + Hotel packages

Top Hotel Deals

See all 104 Hotels in Sheffield Island
DoubleTree by Hilton Norwalk

DoubleTree by Hilton Norwalk

789 Connecticut Ave, Norwalk
    3.5 out of 5.0
     
     

    Situated on the Strip, this hotel is within 3 mi (5 km) of SoNo Switch Tower Museum, Lockwood-Mathews Mansion, and Stepping Stones Museum for Children. Historic ...

    DoubleTree by Hilton Norwalk$95

    DoubleTree by Hilton Norwalk$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
      Glen Cove Mansion Hotel

      Glen Cove Mansion Hotel

      200 Dosoris Ln, Glen Cove
        4.0 out of 5.0
         
         

        This historical estate on Long Island's North Shore Gold Coast features a 1910 Georgian mansion surrounded by 55 secluded and landscaped acres, and includes ...

        Glen Cove Mansion Hotel$145

        Glen Cove Mansion Hotel$145
        The Inn At Fox Hollow Hotel

        The Inn At Fox Hollow Hotel

        7755 Jericho Turnpike, Woodbury
          4.0 out of 5.0
           
           

          Located in the heart of Woodbury, this golf aparthotel is within 3 mi (5 km) of Oyster Bay Golf Course, Oheka Castle, and Plainview Shopping Center. Cold Spring ...

          The Inn At Fox Hollow Hotel$176

          The Inn At Fox Hollow Hotel$176
          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$136

            Doral Arrowwood$136
            Hotel Zero Degrees Norwalk

            Hotel Zero Degrees Norwalk

            353 Main Ave, Norwalk
              3.5 out of 5.0
               
               

              This family-friendly Norwalk hotel is located on a river, within 2 mi (3 km) of Caldor Shopping Center and Gateway Shopping Center. Silvermine Arts Center and ...

              Hotel Zero Degrees Norwalk$129

              Hotel Zero Degrees Norwalk$129
              Comfort Inn Syosset

              Comfort Inn Syosset

              24 Oak Dr, Syosset
                3.0 out of 5.0
                 
                 

                Situated in the business district, this hotel is 2.7 mi (4.3 km) from Plainview Shopping Center and 2.9 mi (4.7 km) from Oyster Bay Golf Course. Broadway Mall ...

                Comfort Inn Syosset$119

                Comfort Inn Syosset$119
                Red Carpet Inn

                Red Carpet Inn

                1209 E Main St, Stamford
                  2.0 out of 5.0
                   
                   

                  Situated near the beach, this hotel is within 1 mi (2 km) of Chelsea Piers and Cove Island Park. Stamford Town Center and Stamford Public Library - Ferguson ...

                  Red Carpet Inn$63

                  Red Carpet Inn$63
                  Oheka Castle Hotel & Estate

                  Oheka Castle Hotel & Estate

                  135 W Gate Dr, Huntington
                    3.5 out of 5.0
                     
                     

                    Situated near the airport, this historic hotel is 2.8 mi (4.4 km) from Oyster Bay Golf Course and within 12 mi (20 km) of Sagamore Hill National Historic Site ...

                    Oheka Castle Hotel & Estate$295

                    Oheka Castle Hotel & Estate$295
                    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

                      Top Flight Deals

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