Amagansett vacation rentals—beautifully furnished, luxury homes

An intimate, storied live-music room—part legendary stage, part casual neighborhood bar—hosting big-name artists alongside East End regulars since 1987. Expect a small, electric crowd, a calendar that turns nightly, and zero pretense; it’s real Hamptons nightlife in a room where the headliner might be leaning on the bar before the set. Visit Stephen Talkhouse

The Amagansett Historical Association preserves a quiet corner of East End history around Miss Amelia’s Cottage (1725), a National Register landmark laid out much as it was kept, with Dominy-crafted furnishings and a rare village-floor view of early Hamptons life. Step through the cottage, then into the Roy K. Lester Carriage Museum behind it for beautifully kept horse-drawn vehicles and local craft. Everything sits right on Main Street for an easy stop between beach and galleries. Visit Amagansett Historical Association

A cluster of boutiques and cafés tucked just off Main Street—shaded paths, Adirondack chairs, and low-key courtyards that invite you to linger. Browse shops, grab something along the way for lunch, and sit under the trees while the afternoon drifts by. It’s a refined, walkable pause with a village feel—easy to fold into any Hamptons day. Visit Amagansett Square

Napeague State Park is a wild, windswept stretch between Amagansett and Montauk—wide, dune-backed beaches on the ocean side and quiet coves along Napeague Harbor. Trails thread through scrub and maritime forest, birdlife is abundant, and the shoreline feels unspoiled and uncrowded. Come for long walks, surf casting, or a calm afternoon by the water; amenities are minimal, the appeal is purity and space. Visit Nepeague State Park

Hither Hills State Park stretches along Montauk’s south shore with miles of dune-backed beach, rolling woodlands, and the famed “walking dunes.” It’s a spacious, unhurried escape that pairs easily with a beach day or a scenic drive to the lighthouse. Visit Hither Hills State Park

Indian Wells Beach in Amagansett is a wide, dune-backed ocean strand with an easy, straight shot from Main Street—ideal for long swims, surf, and unhurried walks. The vibe is polished but low-key; arrive early, especially on sunny weekends, and plan a simple setup (beach chairs, umbrella, a good book). It’s a classic East End beach day—clean shoreline, steady breeze, and an effortless hop to village cafés afterward. Visit Indian Wells Beach

Unwind (or indulge in a pick-me-up) with fair-trade, organic coffee and a vegan pastry in a relaxed yet trendy environment at this local favorite. Visit Jack’s Stir Brew Coffee

Get a casual bite of delicious baked goods with a welcoming vibe, one of the local Hamptonites favorite local spots. Visit Mary's Marvelous

The Meeting House is a polished neighborhood standby—elevated New American plates, a proper martini, and an easy indoor–outdoor rhythm overlooking the green. Recently revived as the culinary extension of The Reform Club, it’s open evenings for a refined, unhurried dinner (with late weekend service), and reservations are simple. Think oysters, a serious burger, seasonal fish, and cocktails done right—exactly the kind of spot you’ll crave. Visit The Meeting House

Discover a curated selection of jewelry, home goods, and accessories emphasizing craftsmanship and originality. Visit Love Adorned

Browse through a diverse mix of surf wear, casual fashion, and locally inspired goods. Visit Lazy Point Variety Store

Luxury fashion known for focusing on modern, minimalist aesthetic. Also offers footwear, accessories, and home goods from established and emerging designers. Visit La Garçonne