The Hamptons Vacation Rentals

Montauk is where the Hamptons feels most wild and ocean-driven, and the coastline here is pure magic. Ditch Plains Beach is a local favorite for surf culture and rolling waves, and the Rheinstein Park trails begin right by the beach entrance for dunes, bluffs, and salty-air views that feel cinematic. 

For big “wow” scenery, Shadmoor State Park delivers dramatic overlooks, and the Montauk Point Lighthouse adds that iconic, end-of-the-island moment that sticks with you long after you leave.

The calmer side of East Hampton lives on the bays, where the water is smooth and the pace slows down instantly. Maidstone Park and Beach in Springs is perfect for a relaxed bay day, with a comfortable shoreline and amenities that make it easy to settle in. 

For classic East End marina atmosphere, Three Mile Harbor is all boats, docks, and golden light, the kind of place where even a simple waterfront stroll feels like a vacation memory.

East Hampton’s villages are made for wandering, charming streets, small shops, galleries, and that “let’s keep walking” feeling. 

Sag Harbor is especially memorable for its waterfront character and historic charm, and the Sag Harbor Whaling & Historical Museum adds depth to the town’s beauty, revealing a sense of history that makes it feel like more than just a pretty place. It’s the kind of spot where you slow down without even realizing it.

A vineyard afternoon is a Hamptons signature, relaxed, sunlit, and quietly indulgent. Wölffer Estate Vineyard in Sagaponack is a standout, with that classic East End vibe that feels instantly iconic. Nearby, Channing Daughters Winery in Bridgehampton offers a more countryside feel, perfect for lingering and letting the day stretch out in the best way.

The Hamptons has a cultural side that makes a stay feel richer than beach days alone. The Parrish Art Museum in Water Mill is an easy, inspiring stop that still feels approachable, even if you are not a “museum person.” 

LongHouse Reserve in East Hampton is a sculpture garden experience where art and landscape blend into a slow, beautiful wander. For something truly local, Guild Hall adds exhibitions and performances right in town, and the Pollock-Krasner House in Springs brings you close to the area’s creative history in a way that feels personal and unforgettable.

Farm stands are a Hamptons ritual, and they make staying in a rental feel especially worth it because the best part comes home with you. Amber Waves in Amagansett has that fresh, local market energy that makes you want to pick up produce, flowers, and “one more” bakery treat. 

Round Swamp Farm is another essential stop, packed with peak-season ingredients and prepared favorites that make an at-home dinner feel elevated without effort.

Dining near East Hampton is all about seafood, seasonal menus, and places that feel like part of the destination. Nick and Toni’s is a classic for a special night out that still feels warm and unfussy. 

For an iconic lunch, The Lobster Roll in Amagansett is a must for its lobster roll legacy, and if you head to Montauk, Duryea’s is known for that waterside setting that turns a meal into a moment. For mornings and take-home treats, Carissa’s The Bakery is the kind of place that makes every breakfast feel like vacation.