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Oak Bluffs: Houses, Condos & More (1,794)

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Additional fees apply. Taxes may be added.
    • 4 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 8
    21
      • 2 BR
      • 1 BA
      • Sleeps 6
        • 2 BR
        • 1 BA
        • Sleeps 4
        14
          • 3 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 6
          3
            • 2 BR
            • 1 BA
            • 1 HF BA
            • Sleeps 4
            1 Review
              • 5 BR
              • 2 BA
              • Sleeps 10
              9
                • 8 BR
                • 5 BA
                • 3 HF BA
                • Sleeps 16
                8
                  • 4 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 11
                  5
                    • 5 BR
                    • 2 BA
                    • Sleeps 12
                    1 Review
                      • 4 BR
                      • 2 BA
                      • Sleeps 8
                      10
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 6
                        8
                          • 3 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 6
                          4
                            • 5 BR
                            • 5 BA
                            • Sleeps 10
                            9
                              • 3 BR
                              • 3 BA
                              • Sleeps 6
                              6
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                7
                                  • 3 BR
                                  • 4 BA
                                  • Sleeps 7
                                  20
                                    • 4 BR
                                    • 3 BA
                                    • 1 HF BA
                                    • Sleeps 10
                                    2 Reviews
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 11
                                      2 Reviews
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 9
                                        3
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 9
                                            • 4 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 10
                                            6
                                              • 6 BR
                                              • 5 BA
                                              • 1 HF BA
                                              • Sleeps 12
                                              1 Review
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 8
                                                11
                                                  • 4 BR
                                                  • 2 BA
                                                  • 2 HF BA
                                                  • Sleeps 9
                                                  3
                                                    • 6 BR
                                                    • 3 BA
                                                    • 1 HF BA
                                                    • Sleeps 12
                                                    8
                                                      • 4 BR
                                                      • 4 BA
                                                      • Sleeps 9
                                                      18
                                                        • 8 BR
                                                        • 3 BA
                                                        • Sleeps 18
                                                        7
                                                          • 6 BR
                                                          • 2 BA
                                                          • 2 HF BA
                                                          • Sleeps 12
                                                          6
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 10
                                                            3
                                                              • 4 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 8
                                                              1 Review
                                                                • 7 BR
                                                                • 4 BA
                                                                • Sleeps 14
                                                                5
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 8
                                                                    • 5 BR
                                                                    • 6 BA
                                                                    • Sleeps 15
                                                                      • 6 BR
                                                                      • 4 BA
                                                                      • Sleeps 14
                                                                      2 Reviews
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 8
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 8
                                                                          18
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 9
                                                                            4
                                                                              • 3 BR
                                                                              • 4 BA
                                                                              • Sleeps 9
                                                                              8
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • 2 HF BA
                                                                                • Sleeps 8
                                                                                7
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 9
                                                                                  2 Reviews
                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 10
                                                                                    8
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      4
                                                                                        • 6 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        33
                                                                                          • 4 BR
                                                                                          • 1 BA
                                                                                          • 2 HF BA
                                                                                          • Sleeps 12
                                                                                          15
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 10
                                                                                              4
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                8
                                                                                                  • 5 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 12
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    4
                                                                                                    • 1 - 50 of 1,794
                                                                                                     

                                                                                                    Recent Oak Bluffs Reviews

                                                                                                    Thoughtfully maintained and close to everything

                                                                                                    5 of 5
                                                                                                    I have been to this home for a few years now and appreciate the thoughtfulness of the owners. They truly do cherish the property and want you to feel at home. It's close to downtown area but far enough that you do relax. Jessica is very attentive and I appreciate that she is always available as a resource. Will be back again with my family.
                                                                                                    • Submitted: Aug 18, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    MV 2016 vacation. Truly gracious hosts. very fast response time from the beginning to the end trip

                                                                                                    5 of 5
                                                                                                    Exquisite property!! Lovely hosts. Very gracious and responsive to any and all inquiries throughout the entire stay. It truly was a beautiful and impeccable property!!! Loved my stay!
                                                                                                    • Submitted: Aug 17, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    Our return trip to Hilltop Haven was even better than year's!

                                                                                                    5 of 5
                                                                                                    Sharon and her team could not be more courteous, accommodating, and genuinely interested in ensuring we had an excellent stay. The home is spacious, comfortable, and perfect for our growing family. I can't recommend staying here highly enough, and we look forward to returning again.
                                                                                                    • Submitted: Aug 15, 2016
                                                                                                    • Stayed: Jul 2016