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Oak Bluffs: Houses, Cottages & More (2,254)

  • 1 - 50 of 2,254
Additional fees apply. Taxes may be added.
    • 1 BR
    • 1 BA
    • Sleeps 2
    2 Reviews
      • 4 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 8
      21
        Wonderful! 4.9/5
        (13 reviews)
        avg/night
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        13
          Wonderful! 4.8/5
          (22 reviews)
          avg/night
          • Studio
          • 1 BA
          • Sleeps 4
          22
            • 4 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 8
            8
              Exceptional! 5.0/5
              (7 reviews)
              avg/night
              • 4 BR
              • 2 BA
              • Sleeps 8
              7
                Wonderful! 4.9/5
                (7 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 3
                7
                  Excellent! 4.6/5
                  (10 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 6
                  10
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    2 Reviews
                      Exceptional! 5.0/5
                      (6 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      6
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        4
                          • Studio
                          • 1 BA
                          • Sleeps 4
                          2 Reviews
                            • 2 BR
                            • 1 BA
                            • Sleeps 6
                            2 Reviews
                              • 5 BR
                              • 2 BA
                              • Sleeps 10
                              10
                                Excellent! 4.3/5
                                (16 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 4
                                16
                                  • 2 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 4
                                  2 Reviews
                                    • 3 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 6
                                    4
                                      Excellent! 4.7/5
                                      (7 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 8
                                      7
                                        • 4 BR
                                        • 4 BA
                                        • Sleeps 22
                                        26
                                          • 3 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 6
                                          5
                                            • 8 BR
                                            • 5 BA
                                            • 3 HF BA
                                            • Sleeps 16
                                            8
                                              Excellent! 4.4/5
                                              (5 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 11
                                              5
                                                Wonderful! 4.8/5
                                                (13 reviews)
                                                avg/night
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 8
                                                13
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 6
                                                  9
                                                    • 5 BR
                                                    • 2 BA
                                                    • Sleeps 12
                                                    2 Reviews
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 6
                                                      6
                                                        • 5 BR
                                                        • 5 BA
                                                        • Sleeps 10
                                                        10
                                                          • 4 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          12
                                                            Wonderful! 4.9/5
                                                            (7 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            7
                                                              Exceptional! 5.0/5
                                                              (31 reviews)
                                                              avg/night
                                                              • 6 BR
                                                              • 3 BA
                                                              • 1 HF BA
                                                              • Sleeps 14
                                                              31
                                                                • 3 BR
                                                                • 4 BA
                                                                • Sleeps 7
                                                                21
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 9
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 11
                                                                    2 Reviews
                                                                      • 5 BR
                                                                      • 4 BA
                                                                      • Sleeps 9
                                                                      3
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        6
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • 2 HF BA
                                                                          • Sleeps 9
                                                                          3
                                                                            • 4 BR
                                                                            • 4 BA
                                                                            • Sleeps 9
                                                                            18
                                                                              • 8 BR
                                                                              • 3 BA
                                                                              • Sleeps 18
                                                                              7
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 8
                                                                                1 Review
                                                                                  • 7 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 14
                                                                                  5
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 10
                                                                                    3
                                                                                      • 6 BR
                                                                                      • 4 BA
                                                                                      • Sleeps 14
                                                                                      2 Reviews
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 8
                                                                                          • 5 BR
                                                                                          • 6 BA
                                                                                          • Sleeps 15
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 8
                                                                                              • 6 BR
                                                                                              • 5 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 12
                                                                                              1 Review
                                                                                                • Studio
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                  Very Good! 4.2/5
                                                                                                  (5 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 6
                                                                                                  5
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 6
                                                                                                    1 Review
                                                                                                      Wonderful! 4.9/5
                                                                                                      (19 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 6
                                                                                                      19
                                                                                                      • 1 - 50 of 2,254
                                                                                                       

                                                                                                      Recent Oak Bluffs Reviews

                                                                                                      The Perfect September Wedding

                                                                                                      5 of 5
                                                                                                      Everything about this house and property was amazing. Darren was a gracious host, helpful and facilitative in the wedding planning process and also there to make sure things went right with the set up during the days prior. The house itself was immaculate and super clean, gorgeous interior and exterior making it the ideal place to stay. If we had any questions about anything Darren was quick to respond. Our wedding was beautiful and so much of that is because we had such a picturesque venue (the ceremony was on the lawn and reception up at the barn). The house is also a great location on the Vineyard, very central. Close to the ferries in Oak Bluffs and Vineyard Haven and a 10 minute drive to Edgartown. Very convenient for my guests and for us to get around the island. Since it's tucked away in the woods you won't hear a car or passer-byers at all. Highly recommend this home for anyone looking to have a more intimate wedding, or just to spend a week in a very tranquil and pretty spot! HUGE thanks to Darren for all of his help and making this amazing place available to us for our special day.
                                                                                                      • Submitted: Sep 25, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Wonderful Stay

                                                                                                      5 of 5
                                                                                                      Everything was more than fine. We thoroughly enjoyed your house and were very comfortable. Our only regret was that we didn't stay longer. I never got to ride one of the bikes. But I did get to swim at South Beach twice, as we were lucky to have beautiful weather for September. The shower on the deck was great, as were the indoor ones. The kitchen was stocked extremely well. Best of all was how clean and comfortable everything was - beds were great. The neighborhood was very private and quiet. Washer and dryer in basement were appreciated. We loved your welcoming committee of 8 turkeys that came strolling out to meet us each time we turned into the driveway. Thank you, Paul, very much for sharing your home with us.
                                                                                                      • Submitted: Sep 24, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Perfect in every way!

                                                                                                      5 of 5
                                                                                                      The House is exactly as promised! Clean, close to everything you want to be near. And Holly and Greg were so wonderful and helpful. We can't wait to come back!!
                                                                                                      • Submitted: Sep 21, 2016
                                                                                                      • Stayed: Sep 2016