Discover the Heartwarming Appeal of an Off-Season Getaway in the Hamptons

Discover the Heartwarming Appeal of an Off-Season Getaway in the Hamptons

This winter season, indulge in a cozy sweater-weather getaway at The Roundtree, Amagansett, a member of the 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 also offered at the luxury boutique hotel.

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 will have visitors experiencing snow dusted vineyards, famed art galleries, world-class wellness, live entertainment, and nights cozied up by a private fireplace.

Included among the many things to do in the area are:

    • A visit to the famous Montauk Lighthouse at Montauk Point State Park
    • Wine tasting 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 will enjoy a luxurious retreat with countless personal touches and thoughtful amenities. Guests can unwind in inviting accommodations, complete with plush bedding, cozy fireplaces and nightly turndown service, with daily continental in-room breakfast included in all overnight visits.  Complimentary afternoon tea, evening snack service, and s’mores and popcorn enjoyed besides welcoming firepits and outdoor heaters in the hotel’s expansive backyard enhance the stay experience. Elevated in-room dinner service offered in courses from the nearby Il Buco Al Mare can also be arranged upon request. 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.