wellfleet vacationYour Landlords - Joy and Bill O'Connor

wellfleet cottage for rentThe O’Connor family has been coming to Wellfleet since 1939 when Great Aunt Deb bought a little cottage right out on the top of the dunes. The views were spectacular, but not wanting to be right at water’s edge, she moved her new home back on the other side of a little dirt road now called Ocean View Drive. And how intuitive the O’Connors were, since that tiny one bedroom cottage would have been long gone into the sea by now if it had stayed where it was. A one-car garage was added (one that opened on both ends because Aunt Deb did not like to back up), and that was turned into a bunkroom for the growing and thriving family. Year after year, the O’Connors spent summers here in Wellfleet, taking turns so that each family would have some time at the cottage.

Seventy years passed by, full of Wednesday night square dancing on the pier, nightly ice cream runs, and hours upon hours of time in the water. We would start in the salt water of the ocean side, riding waves in until, depending on the tides, we would head over to the fresh-water ponds to “clean off”. It was becoming increasingly clear that Wellfleet was where the O’Connors wanted to be. We looked for years, and couldn’t find anything that was just right. It was not until the fourth generation of O’Connors was heading off to college that this hidden piece of property was found. In 2006, the property had been vacant for many years and was in significant disrepair and needed some loving care.

Joy and Bill O’Connor have been purposefully working to restore this 10-acre homestead now affectionately known as Hidden Hollow. First the one-bedroom cottage sitting quaintly by the road, then the three-bedroom cottage with its view of Blackfish Creek…they both were thoughtfully renovated in such a way as to keep the integrity of the old Cape and respect the families who had lived here before.

Currently, with our four children and support of many relatives spanning several generations, we continue to creatively guide the rebuilding of Hidden Hollow. Spending our summers in the Main House, we are available as needed to help make your stay here in Wellfleet as magical as it has been for us over these many years. May you be able to start a tradition that will last from generation to generation and include the beauty, artistry, and uniqueness of the Outer Cape.