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Fairfield Vacations

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

Hotwire can help you find your travel bliss with Fairfield 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 Fairfield

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 Fairfield 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 Fairfield well.

Fairfield Flight + Hotel packages

Top Hotel Deals

See all 131 Properties in Fairfield
The Circle Hotel Fairfield

The Circle Hotel Fairfield

417 Post Road, Fairfield
    3.0 out of 5.0
     
     

    Located in the heart of Fairfield, this hotel is 1.3 mi (2.2 km) from Regina A. Quick Center for the Arts.

    The Circle Hotel Fairfield$105

    The Circle Hotel Fairfield$105
    Best Western Plus Fairfield Hotel

    Best Western Plus Fairfield Hotel

    100 Kings Highway Cutoff, Fairfield
      2.5 out of 5.0
       
       

      Located in the heart of Fairfield, this hotel is within 2 mi (3 km) of Fairfield University, Regina A. Quick Center for the Arts, and Longfellow Park. South ...

      Best Western Plus Fairfield Hotel$102

      Best Western Plus Fairfield Hotel$102
      Hotel Hi-Ho, a Self-Service Property

      Hotel Hi-Ho, a Self-Service Property

      4180 Black Rock Turnpike, Fairfield
        3.0 out of 5.0
         
         

        Situated in Fairfield, this motel is within 1 mi (2 km) of Lake Mohegan and H. Smith Richardson Golf Course. Sacred Heart University and Fairchild Wheeler Golf ...

        Hotel Hi-Ho, a Self-Service Property$105

        Hotel Hi-Ho, a Self-Service Property$105
        The Inn at Fairfield Beach

        The Inn at Fairfield Beach

        1160 Reef Road, Fairfield
          2.5 out of 5.0
           
           

          Offering direct access to the beach, this Fairfield bed & breakfast is within a 10-minute walk of Penfield Beach and Jennings Beach. Fairfield Theater Company ...

          The Inn at Fairfield Beach$165

          The Inn at Fairfield Beach$165
          Omni New Haven Hotel at Yale

          Omni New Haven Hotel at Yale

          155 Temple St, New Haven
            4.0 out of 5.0
             
             

            Combining classic New England style with up-to-date features, this 19-story hotel is one block from the historic New Haven Green and the Shubert Theater and ...

            Omni New Haven Hotel at Yale$167

            Omni New Haven Hotel at Yale$167
            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$214

              Danfords Hotel and Marina$214
              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
                New Haven Village Suites

                New Haven Village Suites

                3 Long Wharf Dr, New Haven
                  3.0 out of 5.0
                   
                   

                  This all-suite hotel is near all downtown New Haven attractions, 1 mile from Yale University, and within 5 miles of Tweed/New Haven Airport. Albertus Magnus ...

                  New Haven Village Suites$122

                  New Haven Village Suites$122
                  La Quinta Inn & Suites New Haven

                  La Quinta Inn & Suites New Haven

                  400 Sargent Dr, New Haven
                     
                     

                    Located in Long Wharf, this hotel is 0.1 mi (0.1 km) from Long Wharf Theatre and 1.7 mi (2.7 km) from Yale University. Knights of Columbus Museum and Wooster ...

                    La Quinta Inn & Suites New Haven$84

                    La Quinta Inn & Suites New Haven$84
                    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, Historic South Norwalk, and Stepping Stones Museum for Children. Lockwood-Mathews ...

                      Top Flight Deals

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