Opened last spring, The Shoals in Southold epitomizes the peninsula’s maritime culture. Located on a marina on Peconic Bay, the 20-suite waterfront hotel houses 20 boat slips, making it accessible by both land and sea. The upscale beach motel-like property is decorated with a mid-century modern, coastal aesthetic throughout. For a fun dining option, The Shoals’ food truck parked on the waterfront lawn alongside picnic tables serves shrimp, lobster rolls, salads, sandwiches, and more from Southold General. Guests also have the option to request a tote bag full of snacks and wine from the gift shop and charter the hotel’s vintage Chris-Craft boat for a day out on the water.
Also in Southold, RICA Bath + Body owner and holistic clinician, Dr. Kristina Ivy, debuted her newest rental bungalow Lake, Sand + Sound in 2022. A mix of boutique hotel, cozy home, and serene spa, these digs are sure to please the wellness-seeker and interior-design lover alike. The 1940s lakeside bungalow—which features an outdoor shower and converted shed for in-suite spa treatments, yoga sessions, and meditation—is decorated in the same style that the RICA storefront in Greenport is loved for, with furnishings, body products, and linen robes from the brand to create a serene space where guests can rest and reset. With two bedrooms, one-and-a-half bathrooms, a full kitchen, and a living room, the house comfortably accommodates up to four guests. Private wine tastings with a local sommelier, a personal chef, and groceries provided upon arrival make your stay extra special.
While Shelter Island was originally a favorite summer retreat for old-money families and notables like Marilyn Monroe, Arthur Miller, and the Kennedys, hoteliers are now turning the tucked-away island into a year-round destination. The Chequit, owned by the same family that recently reopened Peconic Bay Vineyards, reopened last summer after a two-year renovation—just in time to celebrate its 150th anniversary. The hotel’s makeover includes a luxe update to its existing 19 guest rooms, an addition of 16 more, plus a revamp of their famed restaurant The Tavern, now overseen by chef Darren Boyle, formerly at Salt, another notable restaurant on the island. Two new food concepts were also introduced: Weakfish, specializing in New Asian cuisine and Asian-inspired cocktails; and Heights Café, which offers coffee and pastries until mid-afternoon.
The island’s iconic resort, The Pridwin Hotel and Cottages, reopened last July after its own extensive two-year restoration. The property’s full facelift gave the vintage hotel a spirited overhaul while maintaining its spirit of the good old days—it now has a luxe summer camp feel tinged with Dirty Dancing nostalgia. Situated along Crescent Beach overlooking the Peconic Bay, the waterfront hotel is made up of 33 expanded guest rooms and 16 private cottages, complete with warming fireplaces, on almost 10 acres of property. The main house features a full-service spa, a restaurant offering indoor and outdoor dining, and lots of attractive spaces to convene with family and friends. Tennis, yoga on the lawn, kayaking, and stand-up paddle boarding will keep you busy—or, if busyness is what you’re trying to escape, let attendants pamper you at the beach-view pool. Plus, weekly cookouts and s’mores over the campfire add to the summertime vibe. But the fun here isn’t reserved just for the warmer months. The 96-year-old property will be celebrating its second holiday season this winter with decked-out halls and a calendar full of festive cheer.
