The Oak Bluffs Inn is a nine-room inn near Main Street. As of 2011, the inn has a summer rate of at least $225 a night for a room, while in the fall, the lowest cost room is $100. The inn has Wi-Fi and air conditioning in each room and serves a continental breakfast. A small snack bar is available during the afternoon. Many attractions and restaurants, including Sharky's Cantina and the Flying Horses Carousel, are only 1/5 of a mile from the inn.
Isabelle's Beach House is right on the Oak Bluffs beach. Amenities include flat screen TV and free Internet. Six of the inn's 11 rooms have decks. The inn has a two-night minimum stay. The beach house also hosts small conventions, banquets and weddings. Several Oak Bluffs parks, including Waban Park and Niantic Park, are within a ¼ mile of the inn.
The Madison Inn faces the waters of Nantucket Sound, giving guests a view of the waters between Martha's Vineyard and Nantucket. This Oak Bluffs hotel is near the Oak Bluffs public park and most downtown attractions. Right outside the Madison Inn is the Flying Horses Carousel, one of the oldest operating carousels in the United States. Every room at the inn has free Internet, snacks and a flat screen television.
Kathleen's Kottage is a bed and breakfast in Oak Bluffs. Kathleen's Kottage allows pets, including all cats and small dogs. Room amenities vary, and some rooms have kitchens and couches. Rooms have different room layouts. Kathleen's Kottage is 1/4 mile from Island Transport, which offers sightseeing tours to all the major destinations on Martha's Vineyard.