check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 50 of 520
Additional fees apply. Taxes may be added.
    • 2 BR
    • 2 BA
    • Sleeps 6
    67
      • 3 BR
      • 1 BA
      • Sleeps 6
      32
        • 3 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 6
        50
          • 3 BR
          • 2 BA
          • Sleeps 6
            • Studio
            • 1 BA
            • Sleeps 2
            10
              • 1 BR
              • 1 BA
              • Sleeps 4
              12
                • 1 BR
                • 1 BA
                • Sleeps 2
                20
                  • 5 BR
                  • 2 BA
                  • Sleeps 8
                    • 6 BR
                    • 3 BA
                    • Sleeps 15
                    9
                      • 5 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 14
                      8
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        10
                          • 7 BR
                          • 3 BA
                          • Sleeps 16
                          26
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            6
                              • 5 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 9
                                • 3 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 8
                                28
                                  • 4 BR
                                  • 1 BA
                                  • Sleeps 7
                                  5
                                    • 4 BR
                                    • 5 BA
                                    • Sleeps 15
                                    7
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      14
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 4
                                        15
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 5
                                          28
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 2
                                            50
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 7
                                              6
                                                • 3 BR
                                                • 1 BA
                                                • 1 HF BA
                                                • Sleeps 5
                                                11
                                                  • 4 BR
                                                  • 1 BA
                                                  • 1 HF BA
                                                  • Sleeps 7
                                                  21
                                                    • 4 BR
                                                    • 3 BA
                                                    • 1 HF BA
                                                    • Sleeps 8
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                      2 Reviews
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 11
                                                        11
                                                          • 5 BR
                                                          • 7 BA
                                                          • Sleeps 14
                                                          6
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            1 Review
                                                              • 3 BR
                                                              • 1 BA
                                                              • Sleeps 5
                                                                • 4 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 10
                                                                4
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • Sleeps 10
                                                                  5
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    2 Reviews
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      10
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 8
                                                                        6
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 8
                                                                          3
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 3
                                                                            21
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              13
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 10
                                                                                2 Reviews
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 12
                                                                                  3
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 12
                                                                                    20
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 7
                                                                                      1 Review
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        11
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          2 Reviews
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 13
                                                                                            5
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 2
                                                                                              10
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 4
                                                                                                7
                                                                                                  • 3 BR
                                                                                                  • 1 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 8
                                                                                                  10
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 3
                                                                                                    13
                                                                                                    • 1 - 50 of 520
                                                                                                     

                                                                                                    Recent Gloucester and Annisquam Reviews

                                                                                                    Restfull Summerwind Cottage

                                                                                                    5 of 5
                                                                                                    We had a restful and relaxing stay at the Summerwind Cottage. Linda was so kind and answered all our questions. The cottage was clean and fit our family of four to a T. We sat on the patio each morning and watched the fishing boats leave for the day. The sunset were magical for our family to experience, the colors made us long for more. The village was quaint and everyone was so friendly. My wife and I went for a walk each morning all over the village. Good Harbor beach was a family favorite. Would highly recommend the Summerwind Cottage for your family. We will be back!
                                                                                                    • Submitted: Aug 22, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    August Family Reunion

                                                                                                    4 of 5
                                                                                                    We enjoyed our family reunion in your home in Gloucester. The kitchen and front room were wonderful. The owner has prepared a wonderful "home away from home". The only downfall is lack of AC. The windows and multiple fans were helpful, but during a heat wave in August, sleeping upstairs was unbearable. I would recommend the owner purchase some type of portable AC for her guests to be comfortable on those "extra hot" summer nights.
                                                                                                    • Submitted: Aug 21, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    5 bedroom walking distance to Coffins Beach

                                                                                                    5 of 5
                                                                                                    All we can say is WOW! The house is beautiful, with jaw dropping views from almost every window. Short walk to beautiful private Coffins Beach. We stayed for 1 week in August, 6 adults and 4 small children, and there was plenty of room for all. The house is well appointed and has everything you need for a week at the beach. We loved the 2 outdoor showers with hot/cold water. The kids ( and some adults) showered outside every day. Fun, fun fun!
                                                                                                    • Submitted: Aug 13, 2016
                                                                                                    • Stayed: Aug 2016