Weekending in the Hamptons
It’s almost that time again, for long summer weeks and quick weekend escapes to the Hamptons. But not all Hamptons towns are created equal. Each hamlet has its own rhythm and charm, from bohemian to buttoned-up, barefoot to cosmopolitan, and your experience will depend as much on where you stay as what you do. Below is a guide to help you find the perfect pocket of the East End, paired with some of our favorite luxury and boutique hotels.
East Hampton: Cultured, Iconic, and Polished
East Hampton is the crown jewel of the South Fork, offering a blend of quiet affluence, historic architecture, and refined coastal elegance. Picture white clapboard homes behind high hedges, designer boutiques lining Newtown Lane, and art galleries that rival those in Chelsea.
The Maidstone
Just off the village green, The Maidstone is a vibrant boutique hotel with playful, Scandinavian-inspired interiors, an art-filled lounge, and a charming garden patio perfect for morning coffee or evening cocktails. It is ideal for travelers seeking style, walkability, and a splash of whimsy.
The Reform Club
Located in nearby Amagansett, a quieter hamlet within the town of East Hampton, The Reform Club is all about privacy and understated luxury. With lush gardens, spacious suites, and a serene atmosphere, it is perfect for those looking to unplug in elevated surroundings.
Amagansett: Barefoot Luxe with a Creative Edge
Amagansett has a low-key, artistic spirit where surfers, writers, and city escapees gather over wood-fired pizza and vintage wine. It is beachy, cool, and unpretentious, yet home to some of the most thoughtfully curated properties on the East End.
The Roundtree, Amagansett
Tucked along Main Street but hidden behind leafy hedges, The Roundtree is a refined yet relaxed retreat. With modern farm-style cottages, fire pits, and complimentary beach cruisers, it feels like staying at someone’s impeccably designed summer home.
Sag Harbor: Nautical, Historic, and Utterly Charming
Once a bustling whaling port, Sag Harbor is now a sophisticated but easygoing town where yachts line the marina and historic sea captain’s homes have been beautifully preserved. It is literary, diverse, and undeniably charming.
Baron’s Cove
This waterfront gem delivers classic Americana with a maritime twist, including rocking chairs on the porch, harbor views, and cozy rooms with coastal flair. With a lively restaurant, saltwater pool, and walkable access to town, Baron’s Cove is perfect for couples or families who want a bit of everything.
Bridgehampton: Stylish, Central, and All About the Scene
Bridgehampton balances upscale living with laid-back ease. It is home to sprawling horse farms, art fairs, and some of the Hamptons' best food and wine.
Topping Rose House
This standout property is a luxury retreat with a culinary soul. Featuring a Jean-Georges restaurant, chic modern suites, and an outdoor pool surrounded by manicured gardens, it is ideal for travelers seeking full-service amenities and serious gastronomic appeal.
Montauk: Rugged, Laid-Back, and Always Buzzing
Once a humble fishing village, Montauk is now the Hamptons' free-spirited outpost, known for its surf breaks, beach bonfires, and vibrant summer scene. But it has also evolved, offering elevated stays that highlight the natural beauty of "The End."
Gurney’s Montauk Resort & Seawater Spa
Gurney’s is the only luxury hotel in the Hamptons with direct private beach access. With a newly renovated spa, oceanfront dining, and packed summer programming, it is perfect for travelers seeking a full-service resort vibe with unbeatable ocean views.
Ready to Plan Your Weekend Escape?
Whether you are drawn to the cultural charm of East Hampton, the laid-back energy of Montauk, or the historic beauty of Sag Harbor, there is a place in the Hamptons to match your summer mood. Let us help you find the right fit, secure the best rooms, and make your weekend feel effortless from start to finish.
Reach out to start planning your Hamptons escape. The summer calendar is already filling up.
