273 Main St., Amagansett
The Roundtree may be a newish addition to the Hamptons’ hotel scene, but the building itself dates back to the 17th century. Every detail at this meticulously restored property is a nostalgic nod to what we all imagine the Hamptons was like way back when. Traditional clapboard, working fireplaces, brown shingled barns, and a proper s’mores station come nightfall all contribute to a laidback, comfortable vibe. Choose between suites or cottages of various sizes (ideal for those vacationing with kids), take advantage of walking to dinner (hello, Wölffer Kitchen), and chill. Images courtesy of The Roundtree.
The Reform Club
23 Windmill Ln., Amagansett
This luxurious inn with elegant rooms is more of a quiet, art-loving couple's retreat than a family spot. If you're traveling with a group, though, 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.