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!

Narrow Results

Gloucester and Annisquam: Houses, Condos & More (94)

  • 1 - 30 of 94
    • 5 BR
    • 3 BA
    • Sleeps 11
    1 Review
    Request to Book View Details
    24 hrs Confirmation within 24 hours
      • 3 BR
      • 1 BA
      • Sleeps 6
      29
      Request to Book View Details
      24 hrs Confirmation within 24 hours
        • 3 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 6
        47
        Request to Book View Details
        24 hrs Confirmation within 24 hours
          • 6 BR
          • 3 BA
          • Sleeps 15
          8
          Request to Book View Details
          24 hrs Confirmation within 24 hours
            • 5 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 14
            7
            Request to Book View Details
            24 hrs Confirmation within 24 hours
              • 6 BR
              • 3 BA
              • Sleeps 15
              5
              Request to Book View Details
              24 hrs Confirmation within 24 hours
                • 7 BR
                • 3 BA
                • Sleeps 16
                24
                  • 2 BR
                  • 2 BA
                  • Sleeps 4
                  6
                    • 5 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 9
                      • 3 BR
                      • 1 BA
                      • 1 HF BA
                      • Sleeps 9
                      25
                      Request to Book View Details
                      24 hrs Confirmation within 24 hours
                        • 4 BR
                        • 1 BA
                        • Sleeps 7
                        5
                          • 4 BR
                          • 3 BA
                          • Sleeps 7
                          5
                          Request to Book View Details
                          24 hrs Confirmation within 24 hours
                            • 2 BR
                            • 1 BA
                            • Sleeps 5
                            22
                            Request to Book View Details
                            24 hrs Confirmation within 24 hours
                              • 3 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 5
                              10
                              Request to Book View Details
                              24 hrs Confirmation within 24 hours
                                • 4 BR
                                • 3 BA
                                • 1 HF BA
                                • Sleeps 8
                                Request to Book View Details
                                24 hrs Confirmation within 24 hours
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 8
                                  1 Review
                                  Request to Book View Details
                                  24 hrs Confirmation within 24 hours
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 11
                                    11
                                    Request to Book View Details
                                    24 hrs Confirmation within 24 hours
                                      • 2 BR
                                      • 2 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      1 Review
                                      Request to Book View Details
                                      24 hrs Confirmation within 24 hours
                                        • 3 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 8
                                        2 Reviews
                                          • 3 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          5
                                          Request to Book View Details
                                          24 hrs Confirmation within 24 hours
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 8
                                            1 Review
                                            Request to Book View Details
                                            24 hrs Confirmation within 24 hours
                                              • 5 BR
                                              • 6 BA
                                              • Sleeps 16
                                              6
                                              Request to Book View Details
                                              24 hrs Confirmation within 24 hours
                                                • 5 BR
                                                • 2 BA
                                                • Sleeps 13
                                                11
                                                Request to Book View Details
                                                24 hrs Confirmation within 24 hours
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 7
                                                  2 Reviews
                                                  Request to Book View Details
                                                  24 hrs Confirmation within 24 hours
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 7
                                                    2 Reviews
                                                    Request to Book View Details
                                                    24 hrs Confirmation within 24 hours
                                                      • 4 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                      7
                                                      Request to Book View Details
                                                      24 hrs Confirmation within 24 hours
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        1 Review
                                                        Request to Book View Details
                                                        24 hrs Confirmation within 24 hours
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          7
                                                          Request to Book View Details
                                                          24 hrs Confirmation within 24 hours
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            Request to Book View Details
                                                            24 hrs Confirmation within 24 hours
                                                            • 1 - 30 of 94
                                                             

                                                            Recent Gloucester and Annisquam Reviews

                                                            Wow! Spectacular house, spacious yet cozy!

                                                            5 of 5
                                                            This house is a gem! The owner is beyond fantastic and the entire booking process through leaving was amazing. The house is perfectly located in Gloucester with an easy walk or drive to Main St. or the train to Boston. The four-season porch is amazing and a perfect way to unwind at the end of the day. Highly recommend this house for anyone staying on the Northeast coast!
                                                            • Submitted: Apr 23, 2016
                                                            • Stayed: Apr 2016

                                                            Incredible house!!

                                                            5 of 5
                                                            Amazing house with beautiful views! 9 girls stayed for the weekend and we had a blast! Big, awesome kitchen and living group/gathering area for hanging out all together (and even another hang out area on the first floor!) Couldn't have asked for a better house!
                                                            • Submitted: Apr 18, 2016
                                                            • Stayed: Apr 2016

                                                            Spectacular Honeymoon

                                                            5 of 5
                                                            My wife and I had such a wonderful stay on Diamond Avenue for our honeymoon. A beautiful house, beautifully appointed. There is a spectacular view of Ipswich Bay, particularly on the 4th of July. If you are as fortunate as we were, there will be an amazing fireworks competition between 5 guys who live across the bay, and this will last for 2 hours. A short walk to anywhere in the village, and a short drive to the local public beaches and downtown Gloucester. Friendly neighbors; scads of cast iron cookware; comfortable sleeping; ocean sounds; ocean breeze. Cannot recommend this enough.
                                                            • Submitted: Feb 28, 2016
                                                            • Stayed: Jun 2015