Staying in one of Susanne and Wade Green's six 1920s cottages (there's a two-week minimum) or five apartments (with a one-week minimum) feels like crashing the family compound. Rooms are austere affairs (lace duvets, unrenovated bathrooms), but outside, beach chairs, Boogie boards, and all kinds of floating toys are yours to borrow.
The spectacular location on the 'Sconset bluff gives the cottages some of the best views on the island and access to the beach—without the buttoned-up atmosphere of Nantucket's poshest resorts. The cottages are a throwback to an older, saltier Nantucket. Plus, they're only a short jaunt to 'Sconset Market and Claudette's Sandwich Shop—giving guests an off-the-beaten-path feeling within close proximity to 'Sconset village.