When the temperatures drop, the atmosphere in the Hamptons gets cozier. The traffic and crowds are thinner, making late fall and winter the perfect time for a South Fork getaway.
Hotels and inns in the area are still open, ready to welcome guests with hot chocolate, champagne and a warm bed. These seven places left the fireplace on for you.The Maidstone Hotel
The 16 rooms and three cottages in this East Hampton boutique hotel are bright and full of photo art. Renovated in 2017, The Maidstone Hotel’s shared spaces put a whimsical twist on traditional Americana and Hamptons aesthetic. Take the pink sunroom, for example. It’s sure to brighten a dark winter day. As for the onsite restaurant, the menu will have hearty seasonal dishes like soups, steaks and freshly baked pies that remind guests that, amid the hotel’s decorative trimmings, a stay at The Maidstone is snug, not smug. Stay.
Dreary days and the hustle-and-bustle of work is enough to put anyone at their wit’s end. A trip to The End is a perfect cure, even during cooler months. And Gurney’s has established itself as the go-to for rest, relaxation and rejuvenation in Montauk. Though a dip in the Atlantic likely won’t be in the cards, Gurney’s has an ocean-fed indoor seawater pool. Enjoy a swim while taking in panoramic views of the water. The Seawater Spa offers everything from nail services to a head-to-toe ocean radiance massage, which includes a cryogenic seaweed facial mask said to help with reflexology. The relaxation can continue in one of the 146 rooms, cottages and suites. Stay.
Located in the heart of Sag Harbor, this resort has all the makings of luxury: 67 harbor and village-facing rooms, a champagne welcome and a concierge service that can recommend and book activities. But the service is as friendly as it is upscale, making Baron’s Cove feel like a home away from home. The fireplace, located in the entryway, provides warmth even on the coldest of days. Still feeling a chill? The hot toddies served at the bar can solve that. Stay.
The Baker House 1650
This English manor-style East Hampton bed and breakfast blends cozy and luxe for a guest experience that feels part vacation, part staycation. Rooms are equipped with fireplaces and classic clawfoot tubs. Its 17th-century architecture can be seen throughout the grounds. But the amenities, like flat-screen TVs, are decidedly modern. The complimentary spa is the yin to the hotel’s yang. There’s an endless swimming pool, sauna and steam shower that seem unexpected in a bed and breakfast, but those who get their feet wet seldom — if ever — complain. Stay.
The Inn at Windmill Lane
Located three miles from Guild Hall in East Hampton, this chic boutique hotel is an ideal resting spot for those interested in taking in an exhibit at the well-established cultural complex. It’s also a fine place to never leave the room. Guests can make requests, such as food, from the bedroom’s iPad. Each of the seven suites and three cottages is individually decorated. Some mix modern minimalism with homey warmth, and the two-story cottage has expansive east-to-west views of Napeague Harbor. Staycationers can browse and choose the room with decor that suits their styles. Stay.
With only eight rooms, this Sag Harbor hotel is an ideal place for quiet, intimate respite, especially when you consider each room has a whirlpool. The restaurant, set in upscale digs, has an 85-page wine list. If the weather is warm enough, saunter down to the harbor, a three-minute walk, for a taste of summer in winter. Stay.
Topping Rose House
Getting a table at Topping Rose House during the summer is akin to scoring Hamilton tickets or striking gold. But in the off-season, the odds are more favorable. Consider making a weekend of it by staying the night in one of the luxury rooms, suites and cottages — it’ll allow you to have your Prosciutto wrapped pork chops and enjoy the ample wine menu too. Spa services and house vehicles from Lexus are part of the amenity package. Stay.