The last of the Oak Bluff grand dames, the Wesley Hotel was built in 1879 and is comprised of two traditional Victorian buildings. The first hotel outside of Boston to be wired for electricity, the hotel has 95 guest rooms with private baths.
The Wesley is often the first building seen from the harbor or the road. Convenience is one of the hotel's attractions as it's only two blocks from the marina, five minutes from downtown and a five-minute walk to the beaches. Wesley's season typically begins in April or May and ends into October.
For more than 75 years, the Pequot Hotel has been a destination for travelers who want to stay among the colorful, gingerbread cottages. The hotel touts itself as "a lovely, old-fashioned, summer hotel," which is evidenced by its own gingerbread framework, expansive summer porches and rocking chairs.
A complimentary continental breakfast is served every morning before guests walk a block to the beach or the few extra steps to Oak Bluff's shops and restaurants. Afternoon tea and homemade cookies are served on the porch. Guest accommodations include private baths, air conditioning and wireless Internet. The Pequot Hotel is closed in the winter months.
For guests who like to stay in the thick of things, the Oak Bluffs Inn has the desirable location of being in town and centrally situated among abundant shops, restaurants and entertainment. Guests who come by car enjoy free off-street parking, and those who want to enjoy the beach are able to use complimentary beach towels, coolers and beach chairs.
The inn's season typically runs from April through October. Weekend stays must be a two-night minimum in the spring, three nights over the weekend or two-night week stays in the summer season. Fall reservations require a two-night minimum on weekends.
With a mere 14 rooms, the Madison Inn is an intimate boutique hotel. Complimentary snack baskets and free bottled water greet guests in rooms that contain a private bath. Situated in the center of town, the Madison is convenient to all island attractions: town, beaches, marina, gingerbread cottages and the carousel.
Ideal for small weddings or family reunions, the inn is adjacent to a 10-acre park. Travelers can store bicycles in the inn's basement and on-street parking is also available. The hotel's season runs from April through December. Some high-peak stays require a two- or three-night minimum.
