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Westport Vacations

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

Hotwire can help you find your travel bliss with Westport 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 Westport

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 Westport 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 Westport well.

Westport Flight + Hotel packages

Top Hotel Deals

See all 123 Hotels in Westport
The Westport Inn

The Westport Inn

1595 Post Road East, Westport
    2.5 out of 5.0
     
     

    Situated by the ocean, this motel is close to Burying Hill Beach, Sherwood Island State Park, and Country Club of Fairfield. Local attractions also include Westport ...

    The Westport Inn$127

    The Westport Inn$127
    Danfords Hotel and Marina

    Danfords Hotel and Marina

    25 E Broadway, Port Jefferson
      3.5 out of 5.0
       
       

      Located in the heart of Port Jefferson, this spa hotel is steps from Harborfront Park, Maritime Explorium, and Port Jefferson. Theatre Three and Mather House ...

      Danfords Hotel and Marina$186

      Danfords Hotel and Marina$186
      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$109

          Hyatt Regency Greenwich$109
          Red Roof Inn Milford - New Haven

          Red Roof Inn Milford - New Haven

          10 Rowe Ave, Milford
            2.0 out of 5.0
             
             

            Situated in Milford, this motel is within 3 mi (5 km) of Silver Sands State Park, Walnut Beach, and Port Milford. Perry House and National Helicopter Museum ...

            Red Roof Inn Milford - New Haven$72

            Red Roof Inn Milford - New Haven$72
            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
              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
                Hyatt Place Milford / New Haven

                Hyatt Place Milford / New Haven

                190 Old Gate Lane, Milford
                  3.0 out of 5.0
                   
                   

                  Just off highway I-95, Hyatt Place Milford / New Haven is a 5-minute drive from Westfield Connecticut Post shopping mall. Trains from nearby Milford Station ...

                  Hyatt Place Milford / New Haven$113

                  Hyatt Place Milford / New Haven$113
                  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
                    Motel 6 Milford

                    Motel 6 Milford

                    111 Schoolhouse Road, Milford
                      2.5 out of 5.0
                       
                       

                      Situated in the business district, this hotel is within 3 mi (5 km) of Silver Sands State Park, Walnut Beach, and Port Milford. Perry House and National Helicopter ...

                      Motel 6 Milford$77

                      Motel 6 Milford$77

                      Top Flight Deals

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