The 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. We have been coming to Wellfleet for vacations all our lives. For many years Joy and Bill looked to find a place of our own in Wellfleet, but couldn't find anything that was just right. In 2006 this hidden gem was found. At that time the property had been vacant for many years and was in significant disrepair and needed some loving care. We renovated and restored the two rental cottages shortly after we purchased the property and have been enjoying our time as vacation rental owners ever since. We love meeting our new and returning guests, many of whom have been coming back year after year!
What is special about this property?
Since 2006 we 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 (the Road House), then the three-bedroom cottage with its view of Blackfish Creek (Lost Oak Cottage). 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. In 2014 we designed and built the new Tupelo Loft and used the Greek revival design elements from the other houses so that it fit seamlessly onto the property. And finally in 2025, we are renovating the Main House, which is our vacation home.
We fell in love with the location and layout of this property from the first time we saw it. On the ocean side of route 6, we are an easy 1/2 mile walk or bike ride to LeCount Hollow beach. The back of our property has a private entrance to the Cape Cod rail Trail. And the south and east boundaries are protected from any further development by Blackfish creek and the edge of the Cape Cod National Seashore.
What is special about your town?
Wellfleet, Massachusetts, on the Outer Cape, is a quintessential New England seaside town known for its natural beauty, vibrant arts scene, and world-famous oysters. With miles of unspoiled coastline and a rich cultural history, it's the perfect spot for a peaceful, enriching vacation.
In South Wellfleet, the ocean side boasts stunning dunes and pristine beaches. LeCount Hollow Beach, a favorite for beachcombing, surfing, or sunbathing, offers breathtaking Atlantic views. Staying at Hidden Hollow on LeCount Hollow Road puts you close to these beaches and all the town's charm. This serene, cozy retreat offers easy access to the area's best spots.
Start your mornings at PB Boulangerie Bistro, a renowned French bakery offering croissants and fresh pastries. Blue Willow Bakery, another local gem, serves house-made muffins, scones, and coffee in a friendly, welcoming atmosphere—both just steps from Hidden Hollow.
In the evenings, explore Wellfleet's famous art galleries. Known as an artists' haven, the town has galleries featuring everything from contemporary to coastal-inspired art. Many stay open late, making gallery strolls a popular summer pastime.
With its blend of natural beauty, culinary delights, and creative spirit, Wellfleet is a destination that promises relaxation and inspiration. Hidden Hollow is the perfect base for enjoying all the town has to offer.