This winter, indulge in a cozy sweater-weather getaway at The Roundtree, Amagansett, a member of Small Luxury Hotels of the World, where understated luxury meets serene winter landscapes. Take in the tranquility and heartwarming appeal of the Hamptons and enjoy fun-filled days of exploration followed by inspired nights out, all free from the hustle and bustle of the busy summer. What’s more, specialty packages created exclusively for the winter season are offered at the luxury boutique hotel, one of The Hamptons’ most sought-after luxury hotels, just steps from the quaint village of Amagansett, and the ocean.
The award-winning Roundtree, housed within a 100 year-old historic barn, combines luxe travel with thoughtful elements of locality and feelings of home. 14 accommodations celebrate the destination’s farm-steading origins with nature-inspired design within its five standalone cottages and combination of rooms and suites. In addition to those guest rooms, suites and cottages, The Roundtree also boasts a historic Main House and the extensively renovated Beach House, both of which are available for private bookings. (The compound was once owned by legendary playwright Neil Simon, and The Beach House offers access to the members-only Amagansett Beach!)
Whether strolling along snow covered beaches, visiting historic downtown villages, or dining at chic restaurants that are seemingly impossible to get into during the summer months, winter is a wonderful time to explore the world-famous area. This welcoming winter destination invites you to experience snow dusted vineyards, famed art galleries, world-class wellness, live entertainment, and nights cozied up by a private fireplace.
Among the many things to do in the area:
* Visit the famous Montauk Lighthouse at Montauk Point State Park
* Wine taste at the Wölffer Estate Vineyard in Sagaponack
* Discover the Parrish Art Museum in Water Mill
* Shop in style along East Hampton’s Main Street
* Pamper yourself at Naturopathica Spa in East Hampton
* Take a scenic hike through Shinnecock Hills and explore woodlands and nature preserves
* Skate at Buckskill ice rink in East Hampton (with igloo rentals)
* Score a table at Nick & Toni’s in East Hampton
* Enjoy fondue and a live DJ in the Calissa Chalet apres ski-inspired lounge in Watermill
* Listen to live music at the celebrated Stephen Talkhouse in Amagansett
* Explore fine art and special exhibitions at Sotheby’s East Hampton Gallery
* Visit nearby North Fork, known for its wineries, charming small towns, and farmland
Back at The Roundtree, guests enjoy a luxurious retreat with countless personal touches and thoughtful amenities. Unwind in inviting accommodations, complete with plush bedding, cozy fireplaces, and nightly turndown service. Daily continental in-room breakfast is included in all overnight visits. Enjoy complimentary afternoon tea, evening snack service, and s’mores and popcorn. Welcoming firepits and outdoor heaters are found in the hotel’s expansive backyard. And elevated in-room dinner service can be arranged with nearby Il Buco Al Mare, part of NYC’s Il Buco family of famed restaurants. Two seasonal packages are available through March 31, 2025, including the Winter Escape offered at a 20% discount and the Weekly Winter Hamptons retreat starting at $3,000 for a seven-night stay.
If ever a Hamptons getaway was achievable, the time is now.
Photos courtesy of The Roundtree
