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Oak Bluffs: Houses, Cottages & More

  • 1 - 50
Additional fees apply. Taxes may be added.
    NEW!
    • 1 BR
    • 1 BA
    • Sleeps 2
    3
      Wonderful! 4.9/5
      (13 reviews)
      avg/night
      • 4 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 8
      13
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        22
          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
                      (7 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      7
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        3
                          Exceptional! 5.0/5
                          (5 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          5
                            Very Good! 4.2/5
                            (5 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 6
                            5
                              • Studio
                              • 1 BA
                              • Sleeps 2
                                • 5 BR
                                • 2 BA
                                • Sleeps 10
                                10
                                  NEW!
                                  • 2 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 4
                                  3
                                    Excellent! 4.3/5
                                    (16 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    16
                                      • 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
                                              Excellent! 4.4/5
                                              (5 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 11
                                              5
                                                • 8 BR
                                                • 5 BA
                                                • 3 HF BA
                                                • Sleeps 16
                                                8
                                                  Wonderful! 4.8/5
                                                  (13 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  13
                                                    • 5 BR
                                                    • 2 BA
                                                    • Sleeps 12
                                                    2 Reviews
                                                      • 3 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 6
                                                      9
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 6
                                                        6
                                                          • 5 BR
                                                          • 5 BA
                                                          • Sleeps 10
                                                          10
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            13
                                                              Wonderful! 4.9/5
                                                              (7 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              7
                                                                Exceptional! 5.0/5
                                                                (34 reviews)
                                                                avg/night
                                                                • 6 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 14
                                                                34
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • Sleeps 11
                                                                  3
                                                                    • 3 BR
                                                                    • 4 BA
                                                                    • Sleeps 7
                                                                    21
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 9
                                                                        • 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
                                                                              • 8 BR
                                                                              • 3 BA
                                                                              • Sleeps 18
                                                                              7
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • Sleeps 9
                                                                                18
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 8
                                                                                  1 Review
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 10
                                                                                    3
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 14
                                                                                        2 Reviews
                                                                                          • 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
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 6
                                                                                                1 Review
                                                                                                  • Studio
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  2 Reviews
                                                                                                    Wonderful! 4.9/5
                                                                                                    (19 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 6
                                                                                                    19
                                                                                                      • 1 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 4
                                                                                                      8
                                                                                                      • 1 - 50
                                                                                                       

                                                                                                      Recent Oak Bluffs Reviews

                                                                                                      Weekend Wedding

                                                                                                      5 of 5
                                                                                                      Our group of 6 friends stayed here for a weekend for a wedding in the "off season," September 9th-11th. All of us had nothing but wonderful things to say about this house - tons of space, clean and comfortable bedrooms, and plenty of bathrooms/ showers that were greatly appreciated when our large group was getting ready for the wedding. Jessica was very prompt with her replies to our questions and went out of her way to assist us and to make sure we were comfortable. Our first day in the house was unseasonably hot, and Jessica delivered extra fans for us to use as the AC units were already removed at the end of summer. The house does not use a key, but a code box on the door, which actually was really useful for our large group. In terms of location and area, our experience only reflects the "off season." It was about a 15min walk to a main street to access brunch restaurants and grocery store. Otherwise we used cabs and Uber to get around Oaks Bluffs to wedding events.
                                                                                                      • Submitted: Sep 28, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Great week spent on the Vineyard!

                                                                                                      5 of 5
                                                                                                      We absolutely loved our stay at this house! It was beautifully decorated with all of the amenities (and more) that anyone would ever need. The outside space was amazing too - lovely furniture, outside shower, fire pit, hammock and bocce court! The overall location was extremely convenient yet private in a nice neighborhood setting. Like most others, we too have spent many years renting on the Vineyard. This house by far is our favorite! The owner was a pleasure to deal with and always prompt in responding. We would definitely recommend this house to friends/family and hope to get back and enjoy it again!
                                                                                                      • Submitted: Sep 26, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Perfect Wedding Venue!

                                                                                                      5 of 5
                                                                                                      My now husband and I were looking for a venue to host an intimate wedding. We had stopped here to look at the property as a potential venue during one of our vacations and immediately fell in love. The house is secluded and the property is immaculate. Being able to rent the property from Wednesday to Wednesday was perfect. It allowed us to take our time setting up for the wedding and also gave us time to relax after the festivities were over. We invited our bridal party to stay the week with us as a thank you. We had a full house the whole week but never felt overcrowded. The house is gorgeous and I would have been content if we never left the property. We were able to bring in our own vendors which was important to us because we wanted to personalize our wedding as much as we could. We received so many compliments about the wedding and the picturesque location. We had no issues and the owner was very quick to answer any questions we had. If you are looking for a relaxing getaway or a venue that will allow you to make your wedding special, this place is it.
                                                                                                      • Submitted: Sep 26, 2016
                                                                                                      • Stayed: Sep 2016