When visiting Fairfield County Connecticut, be prepared to experience all of the history, culture and natural beauty that Connecticut’s Gold Coast has to offer. Whether you’re staying in a home or apartment overlooking the Long Island Sound or in a lodge deep in the serene beauty of the state parks in the northern section of the county, there are ample opportunities to make your vacation the best yet.

Coastal Fairfield County


Visitors to Coastal Fairfield County can enjoy 30 miles of beautiful coastline that stretch along the picturesque Long Island Sound. Boat docks and yachting clubs abound in the area, as do sandy beaches on which you can soak up some sun. This diverse part of Fairfield County, which includes the exclusive town of Greenwich as well as the less affluent Bridgeport, is highly accessible by train or major highways and provides an abundance of activities and conveniences for travelers and residents in the area.

If the superb restaurants and shops in the area aren’t enough, a short train ride or drive will put you in the heart of New York City. Most vacation rental homes in the area are a short walk to a nearby train station.

Northern Fairfield County


If you prefer a slower pace and a closer communion with nature, the northern part of Fairfield County may be to your liking. You might think you’re in a completely different state when you arrive in the area as the terrain changes from shoreline to foothills.

While fine dining and shopping is still available in the area, your focus may be on enjoying the quiet and scenic surroundings. Activities include golfing, horseback riding, skiing, fishing, and boating. Towns surrounding Candlewood Lake offer a quaint haven where vacationers can enjoy life at an unhurried pace.

Whether you prefer to stay in a vacation rental on the shore or farther north in towns like New Milford, Ridgefield and Sherman (voted Connecticut’s #1 Small Town multiple times), Fairfield County has the vacation destination that is right for you.

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Fairfield County: Houses, Cottages & More(86)

86 Results
  • 3 BR,
  • 2 BA,
  • Sleeps 6
#933104
    7 night minimum stay
    • 3 BR,
    • 1 BA,
    • Sleeps 8
    #399830
      7 night minimum stay
      • 1 BR,
      • 1 BA,
      • Sleeps 6
      #3748841
      30 - 31 night minimum stay
      • 4 BR,
      • 3 BA,
      • Sleeps 8
      #372153
      (6)
        2 night minimum stay
        • 4 BR,
        • 4 BA,
        • 1 HF BA,
        • Sleeps 11
        #414885vb
          2 night minimum stay
          • 2 BR,
          • 1 BA,
          • 1 HF BA,
          • Sleeps 4
          #3473505
          (4)
          3 night minimum stay
          • 1 BR,
          • 1 BA,
          • Sleeps 4
          #3465310
          (4)
          3 - 4 night minimum stay
          • 3 BR,
          • 1 BA,
          • Sleeps 5
          #3024325
          (4)
          $295 - $600
          per night
          3 night minimum stay
          • 4 BR,
          • 2 BA,
          • Sleeps 9
          #987250
          (3)
          3 - 6 night minimum stay
          • 4 BR,
          • 4 BA,
          • Sleeps 12
          #3673376
          2 night minimum stay
          • 3 BR,
          • 2 BA,
          • Sleeps 8
          #3681469
          4 night minimum stay
          • 3 BR,
          • 2 BA,
          • Sleeps 7
          #3728950
          2 night minimum stay
          • 2 BR,
          • 3 BA,
          • Sleeps 6
          #580305vb
          4 night minimum stay
          • 4 BR,
          • 1 BA,
          • Sleeps 8
          #3749757
          2 night minimum stay
          • 5 BR,
          • 5 HF BA,
          • Sleeps 7
          #3020319
          2 Reviews
          7 - 30 night minimum stay
          • 3 BR,
          • 2 BA,
          • Sleeps 6
          #417322vb
          (9)
            2 - 7 night minimum stay
            • 3 BR,
            • 2 BA,
            • Sleeps 4
            #159815
            2 Reviews
              14 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 6
              #3674316
                2 night minimum stay
                • 3 BR,
                • 2 BA,
                • Sleeps 6
                #130517
                (7)
                  2 night minimum stay
                  • 1 BR,
                  • 1 BA,
                  • Sleeps 2
                  #471970vb
                  1 Review
                    14 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • Sleeps 7
                    #181120
                    2 Reviews
                      2 night minimum stay
                      • 1 BR,
                      • 1 BA,
                      • 1 HF BA,
                      • Sleeps 4
                      #3485851
                      (7)
                        2 - 7 night minimum stay
                        • 5 BR,
                        • 4 BA,
                        • 1 HF BA,
                        • Sleeps 12
                        #3520704
                          7 - 30 night minimum stay
                          • 3 BR,
                          • 1 BA,
                          • Sleeps 6
                          #327984
                          (4)
                            2 night minimum stay
                            • 3 BR,
                            • 3 BA,
                            • Sleeps 8
                            #3527775
                              7 night minimum stay
                              • 4 BR,
                              • 3 BA,
                              • 1 HF BA,
                              • Sleeps 10
                              #3002646
                                4 night minimum stay
                                • 4 BR,
                                • 4 BA,
                                • 2 HF BA,
                                • Sleeps 8
                                #3543628
                                1 Review
                                  14 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 8
                                  #121514
                                    2 - 7 night minimum stay
                                    • 5 BR,
                                    • 3 BA,
                                    • 1 HF BA,
                                    • Sleeps 10
                                    #257571
                                    (8)
                                      10 - 14 night minimum stay
                                      • 5 BR,
                                      • 3 BA,
                                      • Sleeps 10
                                      #337707
                                      1 Review