Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

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 Hotels 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 1.4 mi (2.2 km) from Regina A. Quick Center for the Arts.

    The Circle Hotel Fairfield$89

    The Circle Hotel Fairfield$89
    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 ...

      Hotel Hi-Ho

      Hotel Hi-Ho

      4180 Black Rock Turnpike, Fairfield
        3.0 out of 5.0
         
         

        Situated in Fairfield, this motel is 1.2 mi (1.9 km) from H. Smith Richardson Golf Course and 2.7 mi (4.3 km) from Fairchild Wheeler Golf Course. Fairfield University ...

        Hotel Hi-Ho$89

        Hotel Hi-Ho$89
        The Inn at Fairfield Beach

        The Inn at Fairfield Beach

        1160 Reef Road, Fairfield
          2.5 out of 5.0
           
           

          Situated by the ocean, this bed & breakfast is within 1 mi (2 km) of Penfield Beach, Jennings Beach, and Fairfield Theater Company. Fairfield Museum and History ...

          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 ...

            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 ...

              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$67

                Motel 6 Milford$67
                EVEN Hotel Norwalk

                EVEN Hotel Norwalk

                426 Main Ave, Norwalk
                  3.5 out of 5.0
                   
                   

                  Situated in the business district, this hotel is within 1 mi (2 km) of Caldor Shopping Center and Gateway Shopping Center. Silvermine Arts Center and Norwalk ...

                  EVEN Hotel Norwalk$85

                  EVEN Hotel Norwalk$85
                  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$107

                    Hyatt Regency Greenwich$107
                    Holiday Inn Express & Suites Milford

                    Holiday Inn Express & Suites Milford

                    278 Old Gate Ln, Milford
                      2.5 out of 5.0
                       
                       

                      Situated in Milford, this hotel is 0.7 mi (1.1 km) from Westfield Connecticut Post Mall and within 3 mi (5 km) of Robert Treat Farm and Port Milford. PEZ Visitor ...

                      Top Flight Deals

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