When most people think of the Hamptons, summer crowds and sun-soaked beaches come to mind. But those in the know understand that winter reveals the region’s most enchanting side—quiet, intimate, and effortlessly elegant. Nowhere is this more evident than at The Roundtree, Amagansett, an award-winning boutique hotel and member of Small Luxury Hotels of the World.
Set on a serene two-acre property just steps from Amagansett Village and moments from the ocean, The Roundtree offers a refined yet welcoming retreat designed for travelers seeking understated luxury. With only 14 accommodations—including rooms and suites housed in a beautifully restored 100-year-old barn, five standalone cottages, and a historic Main House—the property feels more like a private residence than a traditional hotel.
Each space is thoughtfully curated with natural textures, plush bedding, cozy fireplaces, and a soothing neutral palette inspired by the surrounding landscape. The result is a stay that feels elevated yet deeply personal—perfect for romantic getaways, creative retreats, or a restorative winter escape.
What truly distinguishes The Roundtree is its attention to detail and heartfelt hospitality. Guests are treated to a daily continental in-room breakfast, complimentary afternoon tea, evening snacks, and nightly turndown service. As temperatures drop, the property comes alive with outdoor firepits, heaters, and seasonal favorites like s’mores and popcorn—small touches that create a sense of warmth and nostalgia. For an elevated dining experience, guests can arrange in-room, multi-course dinners sourced from the renowned Il Buco Al Mare.
Winter in the Hamptons offers a slower, more soulful pace, and The Roundtree serves as the perfect home base for exploration. Guests can enjoy snow-dusted beach walks, wine tastings at nearby Wölffer Estate Vineyard, or cultural outings to the Parrish Art Museum and Sotheby’s East Hampton Gallery. Wellness lovers will appreciate visits to Naturopathica Spa, while evenings can be spent enjoying live music at the iconic Stephen Talkhouse or securing coveted reservations at beloved local restaurants—without the summer waitlists.
The Roundtree’s seasonal offerings make an off-season stay even more appealing. Winter Escape and Weekly Winter Hamptons packages provide exclusive rates and extended-stay options, inviting guests to truly settle in and experience the East End at its most authentic.
Whether you’re seeking a peaceful weekend away or a longer winter retreat, The Roundtree, Amagansett delivers a rare blend of luxury, tranquility, and genuine comfort. It’s a reminder that the Hamptons aren’t just a summer destination—they’re a year-round state of mind.
Plan your winter escape and discover off-season Hamptons magic at
www.theroundtreehotels.com
