128 Main Street
Located just outside of downtown Edgartown and not far from the beach, Hob Knob has provided lodgings for generations of travelers, including Senator John F. Kennedy during a Vineyard sailing regatta in 1947.
The 19th-century Gothic revival hotel has 16 guest rooms, a deluxe suite and two private houses available for weekly rentals. All have private baths, king-sized beds and free wi-fi. There is also a fitness center with sauna and steam room and spa with certified massage therapists. Eco-friendly practices include the use of local, organic foods, kitchen composting, in-room recycling, a water-saving linen reuse program and glass water bottles.