Luxury holidays rental Osterville, United States

Renovated and decorated by a renowned Island decorator, and featured in Architectural Digest thereafter, this gem sits on a rather unique piece of property overlooking the historic Edgartown harbor. Located on the north side of town, the views are of the immediate harbor as well as the north bluff of Chappaquiddick; during sunrise or sunset the exquisite coloration cast off the harbor is a guaranteed inspiration. With three comfortable bedrooms and flowing open common areas, this home is your ideal vacation spot. Discerningly decorated in nautical theme, it has an old world charm with all the modern conveniences. Located a block from all downtown Edgartown amenities, including Fuller Street Beach. $6,000-$25,000/week

Nestled in the heart of Edgartown Village, this renovated Captain's home seamlessly combines historic charm with modern elements, resulting in a truly captivating residence. The main house spans four floors, providing expansive living spaces. Stepping onto the private covered porch, one is greeted by the warmth of an inviting porch, wood-burning fireplace and breathtaking views of the exquisitely landscaped grounds. This exceptional property encompasses over 7,000 square feet of thoughtfully designed living space, making it an ideal in-town compound, spacious and comfortable home for hosting family and friends. Adjacent to the main house stands a detached two-story Carriage House, which adds another layer of luxury and functionality to the property. A pool cabana provides a convenient space for relaxation. The private outdoor living area, complete with a gunite pool, built-in whirlpool spa, and a serene bluestone terrace, is ideal for lounging poolside. $20,000 - $35,000/week