Amagansett Hotels

Traditional clapboard, working fireplaces, and brown shingled barns all contribute to the Roundtree’s laid-back, comfortable vibe. Choose between suites or cottages of various sizes (ideal for those vacationing with kids), take advantage of room service from Il Buco Al Mare and walking-distance lunches at Doubles, and chill.

This luxurious inn with spare, elegant rooms, soaring ceilings, tiled fireplaces, and super-indulgent bathrooms is a quiet retreat that’s private enough to work as a couples’ or family getaway. The comfy living areas are stocked with thoughtful snacks and strewn with coffee-table books. The gardens are beautiful—perfect for a wedding or gathering. If you're traveling with a group, ask about 21 House, the four-bedroom private home, which comes with all the amenities of the larger inn (housekeeping, gym, transportation) and is available for private rentals. They're hosting a pop-up of Manhattan and LA's Remedy Place in August.