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  • 1 - 50 of 283
    • 2 BR
    • 2 BA
    • Sleeps 6
    68
      • 3 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 6
      50
        • 3 BR
        • 1 BA
        • Sleeps 6
        32
          • 3 BR
          • 2 BA
          • Sleeps 6
            • Studio
            • 1 BA
            • Sleeps 2
            13
              • 4 BR
              • 5 BA
              • Sleeps 15
              8
                Wonderful! 4.8/5
                (13 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 4
                13
                  • 5 BR
                  • 2 BA
                  • Sleeps 8
                  1 Review
                    • 5 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 14
                    8
                      • 6 BR
                      • 3 BA
                      • Sleeps 15
                      11
                        Wonderful! 4.8/5
                        (10 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        10
                          • 2 BR
                          • 2 BA
                          • Sleeps 4
                          6
                            • 7 BR
                            • 3 BA
                            • Sleeps 16
                            26
                              • 5 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 9
                                Wonderful! 4.8/5
                                (29 reviews)
                                avg/night
                                • 3 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 8
                                29
                                  Exceptional! 5.0/5
                                  (5 reviews)
                                  avg/night
                                  • 4 BR
                                  • 1 BA
                                  • Sleeps 7
                                  5
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    21
                                      • 3 BR
                                      • 3 BA
                                      • 1 HF BA
                                      • Sleeps 8
                                      3
                                        • 4 BR
                                        • 1 BA
                                        • 1 HF BA
                                        • Sleeps 10
                                        4
                                          • 3 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          7
                                            Excellent! 4.7/5
                                            (6 reviews)
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 7
                                            6
                                              • 3 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 5
                                              12
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 5
                                                28
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  52
                                                    • 4 BR
                                                    • 1 BA
                                                    • 1 HF BA
                                                    • Sleeps 7
                                                    22
                                                      • 4 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        2 Reviews
                                                          Wonderful! 4.8/5
                                                          (12 reviews)
                                                          avg/night
                                                          • 4 BR
                                                          • 2 BA
                                                          • Sleeps 11
                                                          12
                                                            • 5 BR
                                                            • 7 BA
                                                            • Sleeps 14
                                                            6
                                                              • 3 BR
                                                              • 1 BA
                                                              • Sleeps 5
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 3
                                                                21
                                                                  Wonderful! 4.9/5
                                                                  (15 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  15
                                                                    Exceptional! 5.0/5
                                                                    (12 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    12
                                                                      NEW!
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                        Exceptional! 5.0/5
                                                                        (15 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        15
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 3
                                                                          16
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            5
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 12
                                                                              21
                                                                                Excellent! 4.7/5
                                                                                (6 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 13
                                                                                6
                                                                                  • 5 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 12
                                                                                  24
                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 10
                                                                                    2 Reviews
                                                                                      Excellent! 4.6/5
                                                                                      (12 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      12
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        3
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 12
                                                                                          5
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            4
                                                                                              • 4 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 8
                                                                                              3
                                                                                                • 5 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 13
                                                                                                17
                                                                                                  Exceptional! 5.0/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 4
                                                                                                  9
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 5
                                                                                                    4
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 7
                                                                                                      1 Review
                                                                                                      • 1 - 50 of 283
                                                                                                       

                                                                                                      Recent Gloucester and Annisquam Reviews

                                                                                                      Great house for groups with fenced in yard!

                                                                                                      4 of 5
                                                                                                      A group of friends and I stayed here while we attended a Gloucester wedding for the weekend. There's a beautiful grassy fenced in yard with horseshoe pits, firepit and plenty of seating. The house is in good shape with 5 bedrooms (3 in upstairs apartment and 2 in downstairs apartment, both with kitchens and living rooms and pretty comfy beds. The location was a quick walk to the beach and a 2 min drive to the grocery store so you have just about everything you need! There is construction going on in the lot next door but nobody was working on it while we were there. Lisa was prompt in communication and helpful when I had questions. There was some confusion over what was covered in linen rental and she was amenable and helped us get situated. The only downside is that linens are not included and to rent them was overly expensive at $250. It worked out okay because we were 5 couples, 3 of which were traveling from out of town so packing them would have been annoying, but still $50/couple for a set of sheets and bath towels (beach towels are not included) seems very expensive to me. And it's not like they're through a rental company as the owners set you up themselves (and in our case one of the beds didn't have set of sheets that fit so we had to scrounge another flat sheet). Overall the stay was really great, Lisa is a communicative and helpful owner, and we would be happy to return though we would definitely not pay for linens.
                                                                                                      • Submitted: Sep 21, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Wingaersheek Beach House

                                                                                                      5 of 5
                                                                                                      The property was great! A quiet setting that met all expectations for our family get-together. Having our morning coffee and enjoying the fantastic views was a relaxing start to our days. The kitchen was great, with everything needed and added to the "home-like" feeling for our stay. We also enjoyed the 2-level living that gave everyone their space. The kayaks, beach equipment, video games, etc would make this a great stay for families with teens.The owners were very helpful with suggestions for dinning & shopping. Instructions for house operation were clear and appreciated. With each spectacular sunrise/sunset, our family voted this house a five star selection and highly recommended!
                                                                                                      • Submitted: Sep 20, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Beautiful views, relaxing vacation

                                                                                                      5 of 5
                                                                                                      We had an amazing time. The view from the house was beautiful. Dont miss the low tides which are quite dramatic. We were able to walk all over the mash and see egrets and herons close up or as much as they would allow. Sat out on the floating dock almost every evening to watch the sunset. would love to go back,
                                                                                                      • Submitted: Sep 20, 2016
                                                                                                      • Stayed: Sep 2016