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Oak Bluffs: Houses, Cottages & More (2,745)

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    • 3 BR
    • 2 BA
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    • Sleeps 6
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        • 4 BR
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            • 4 BR
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            18
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              • 3 BR
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              • Sleeps 6
              6
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                • 2 BR
                • 1 BA
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                  • 3 BR
                  • 1 BA
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                  • Sleeps 6
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                    • 4 BR
                    • 3 BA
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                    • Sleeps 10
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                      • 5 BR
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                      8
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                        • 6 BR
                        • 3 BA
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                        • Sleeps 14
                        22
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                          • 6 BR
                          • 3 BA
                          • 1 HF BA
                          • Sleeps 12
                          8
                            • 8 BR
                            • 5 BA
                            • 3 HF BA
                            • Sleeps 16
                            5
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                              • 8 BR
                              • 3 BA
                              • Sleeps 18
                              7
                                • 5 BR
                                • 5 BA
                                • Sleeps 10
                                3
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                                  • 3 BR
                                  • 4 BA
                                  • Sleeps 7
                                  17
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                                    • 5 BR
                                    • 5 BA
                                    • Sleeps 15
                                    3
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 6
                                      7
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                                        • 6 BR
                                        • 6 BA
                                        • 2 HF BA
                                        • Sleeps 15
                                        2 Reviews
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          4
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                                            • 9 BR
                                            • 7 BA
                                            • 2 HF BA
                                            • Sleeps 24
                                            3
                                              • 6 BR
                                              • 2 BA
                                              • 2 HF BA
                                              • Sleeps 12
                                              6
                                                • 2 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 8
                                                  • 5 BR
                                                  • 2 BA
                                                  • Sleeps 10
                                                  3
                                                    • 6 BR
                                                    • 4 BA
                                                    • Sleeps 14
                                                    2 Reviews
                                                      • 4 BR
                                                      • 4 BA
                                                      • Sleeps 9
                                                      17
                                                        • 2 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 4
                                                        3
                                                          • 4 BR
                                                          • 2 BA
                                                          • Sleeps 10
                                                          3
                                                            • 7 BR
                                                            • 4 BA
                                                            • Sleeps 14
                                                            4
                                                            • 1 - 30 of 2,745
                                                             

                                                            Recent Oak Bluffs Reviews

                                                            Wow! Highly recommend this Vineyard estate!

                                                            5 of 5
                                                            This property is gorgeous. It far surpassed our expectations. My family enjoyed sun-filled days at the pool - which has a great baja shelf for smaller children to enjoy, and relaxing evenings on the patio where we enjoyed many meals together. The outdoor spaces are beautiful and it was such a treat to enjoy dinner and wine in the outdoor dining area! The home is well appointed with every amenity you could possibly need. Lots of space to spread out, beautiful furnishings, very clean, and plenty of places to sleep. The bunk beds are amazing and so comfortable. The common areas are family-friendly and comfortable, we absolutely loved spending this trip together as a family in this home. We will never forget our time here and cannot wait to book again. The owner and caretaker were so nice, attentive, and helpful. The process was easy and smooth... 5 STARS! Highly recommend!
                                                            • Submitted: Apr 25, 2016
                                                            • Stayed: Jun 2015

                                                            So convenient to everything!

                                                            5 of 5
                                                            I've stayed at this house, off and on, for many years now. You can't beat the location. The owners are fantastic to work with and so responsive. Last time we visited, we didn't even bother with a car (and the ferry was booked anyway). We would hop over to the beach, and then we would head back to the house for lunch. Later we walked into town to grab dinner. There was a mix of adults and kids in our party and it all worked out well. Some shopping, some explored, some went to the park to fly kites, play tennis, shoot hoops. It's all there. We did take our bikes over and that was great. The house has everything, is clean and uncluttered. It's nice to have linens included, so we didn't have to bring those over. Can't wait to come back! Almost don't want to share it because I want to keep this find all to myself!
                                                            • Submitted: Mar 28, 2016
                                                            • Stayed: Jun 2015

                                                            The PERFECT setting for our September wedding!

                                                            5 of 5
                                                            My wife and I rented this property for a week and had our wedding during our stay. We put our entire wedding party in the house and even had our rehearsal dinner there. I could write a long essay about why this was the perfect venue for every aspect of our trip, our rehearsal dinner, our wedding, our reception. From what I understand a lot of people use barn for any of the above activities but with the perfect fall MV weather we did not want a roof over our head. With prior permission we used the expansive yard. We used the small green opening to the right of the house (when looking towards it from the circle drive) with a wooded backdrop for our pre-ceremony cocktail our and our ceremony. We used the patio and grassy area to the left of the house for our cocktail hour (complete with raw bar) and we used the large flat grassy area behind (and to the left) of the home for the dinner/reception. It was perfect and amazing. The expansive and diverse grounds give you plenty of photo ops and our photographers were floored by everything - we made their "best of" post and constantly got compliments on how great the venue was. Can't say enough great things. Of course, last but not least, Darren was really wonderful to work with and really went above and beyond. Thank you very much! Chris & Crystal
                                                            • Submitted: Feb 12, 2016
                                                            • Stayed: Sep 2015