Built in 1872, the Chequit Inn is a gracious Victorian country inn with thirty-five guest rooms in three adjacent buildings and several common areas. The Chequit's porch and tree-shaded patio afford guests a wonderful view of the seascape, landscape, and downtown streetscape of Shelter Island Heights. The Chequit has a large, elegant dining room on the main level.

In addition, The Catchall, a completely renovated bistro-style restaurant in the Inn's lower level, is a popular gathering place for islanders and visitors alike. Colorful animal murals uncovered during the Catchall's renovation adorn the entrance, and there is a comfortable, relaxing atmosphere throughout. Sporting events, news, and other programs of interest may be on view on the Catchall's 55" screen TV, and there is a jukebox and a pool table.

Half of the Chequit's rooms are located in the Inn's main building. Additional accommodations are available during the summer months in the Cedar House and the Summer Cottage, buildings which are adjacent to the Chequit's main building.

Additional accommodations and amenities are available at the Chequit Inn's sister inns, the Ram's Head Inn and the Captain Bennett House. The tennis court, private beachfront, boats, and fitness room at the Ram's Head Inn are available to guests of the Chequit Inn and Captain Bennett House.