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Old Greenwich Vacations

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

Hotwire can help you find your travel bliss with Old Greenwich 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 Old Greenwich

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 Old Greenwich 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 Old Greenwich well.

Old Greenwich Flight + Hotel packages

Top Hotel Deals

See all 167 Hotels in Old Greenwich
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
    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$131

      Royal Regency Hotel$131
      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
        Extended Stay America - Long Island - Melville

        Extended Stay America - Long Island - Melville

        100 Spagnoli Rd, Melville
          2.5 out of 5.0
           
           

          Situated near the airport, this hotel is within 2 mi (3 km) of Adventureland, Farmingdale State College, and Old Bethpage Village Restoration. American Airpower ...

          Extended Stay America - Long Island - Melville$121

          Extended Stay America - Long Island - Melville$121
          La Quinta Inn & Suites Garden City

          La Quinta Inn & Suites Garden City

          821 Stewart Ave, Garden City
            2.5 out of 5.0
             
             

            Located in Garden City, an upscale suburban community, this hotel is a half-mile from the Roosevelt Field mall and 3 miles from the Nassau Coliseum. Train stations, ...

            La Quinta Inn & Suites Garden City$101

            La Quinta Inn & Suites Garden City$101
            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$144

              DoubleTree by Hilton Tarrytown$144
              Red Roof PLUS+ Long Island - Garden City

              Red Roof PLUS+ Long Island - Garden City

              699 Dibblee Drive, Westbury
                2.5 out of 5.0
                 
                 

                This Long Island hotel puts guests a 15-minute drive from Jones Beach, the most heavily visited stretch of Atlantic-facing sand on the East Coast. Roosevelt ...

                Red Roof PLUS+ Long Island - Garden City$115

                Red Roof PLUS+ Long Island - Garden City$115
                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 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
                    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

                      Top Flight Deals

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