Play on the pétanque courts after enjoying pastries and bread baked in house at the two-year-old La Maison Blanche Hotel (from $275), located in the residential Shelter Island Heights district. Though the building dates back to the 1800s, its eleven guest rooms feel contemporary thanks to beach-inspired décor, 400-thread-count linens, and Côté Bastide bath products. There’s also a perfectly nice pool here, but it’s better to borrow one of the free bicycles and ride over to nearby Crescent Beach.
Cook your own dinner on the outdoor barbecues at the family-friendly Dering Harbor Inn (from $300; two-night minimum), which offers units ranging from studios to two-bedroom villas, all with private decks or screened-in porches. Located on seven acres overlooking the picturesque harbor, the property also offers a pool, fitness center, tennis courts, and waterfront beach; plus, it’s just a five-minute walk to the main village.
Wake up to the sound of crashing waves at Sunset Beach (from $625), André Balazs’s stylish haven that draws travelers looking for a little bit of Hamptons-style glitz. Fortunately, the hotel’s size—twenty rooms—keeps things relatively calm, and each one features a private balcony overlooking the ocean and Crescent Beach, the best sunset vantage point on the island.