The Historic Building uses mahogany, polished brass, and oak-leaf motifs to reference the island's maritime character, with cobalt-blue walk-in showers in the bathrooms. Views vary between water, village, and resort. The Roxana borders the gardens and pool, with balconies or patios and a brighter palette accented in red. Its outlooks include the Great Lawn, pool, and Edgartown village.
The Captain's Cottages contain 28 individual units, including one- to three-bedroom suites with kitchenettes and living rooms. A one-bedroom layout has a king bed and a queen sofa bed. Standard two-bedroom cottage suites have queen bedrooms, two bathrooms, and a semi-private porch. On the Historic Building's fourth floor, the Presidential Skyhouse has one bedroom, a kitchen, dining room, outdoor deck, and guest half bath. The separate Sky Family Suite has a king bedroom, a bunk room sleeping four children, and one bathroom. The Sky Guest Room has a king bed and dressing room. Each has its own key within a shared entrance, and reserving all three creates a private Skyhouse Wing.