A Long Island vacation is often synonymous with the Hamptons—but what if you could have beautiful vistas and hydrangea-lined streets without the crowds? The Pridwin on Shelter Island and Baron’s Cove in Sag Harbor—both owned and operated by Cape Resorts—are lesser-known and quieter, but just as special.
The Pridwin Hotel & Cottages
Shelter Island, Long Island
Shelter Island feels like a distant coastal New England destination but it’s surprisingly accessible from Westchester—about a three-hour drive, plus a brief ride on the car ferry from either Greenport or North Haven. The journey to the historic Pridwin Hotel and Cottages is well worth it, and the timeless allure of the property offers endless ways to indulge in oceanside relaxation.
Situated on 10 acres, The Pridwin overlooks spacious Crescent Beach. For nearly 100 years, this retreat—named after King Arthur’s shield—has treated vacationers to a full slate of entertainment and watersports, accommodations in a range of hotel rooms and cottages, and myriad dining options in a quaint setting that’s reminiscent of classic Catskills resorts.
Renovated and reopened in 2022 under the care of its new owner, Curtis Bashaw of Cape Resorts, The Pridwin boasts luxurious guest rooms with modern amenities yet continues to exude old-world charm: the library and game room, nautical flourishes throughout the property, white-washed Adirondack chairs on the front lawn, and 16 cozy cottages—each with a kitchenette, private deck, and gas fireplace.
For even more relaxation, hit the spa for an afternoon of self-care. Opt for a facial with organic, seaweed-based products, a custom massage, or indulge in a full-body sea salt exfoliation treatment.
For a more active stay, the Pridwin has both tennis and pickleball courts, complimentary bikes available for cruising around the island, and a network of scenic hiking trails though the 2,350-acre Mashomack Preserve.
The Pridwin’s season runs through Labor Day with rates from $400/night for the hotel, $710/night for the cottages.
Baron’s Cove
Sag Harbor, Long Island
To get the full upscale Hamptons experience, but with a quiet, small-town appeal, Baron’s Cove in Sag Harbor offers the perfect middle ground. The harborside inn, tucked away within the privacy of the cove, is a short walk from the boutiques, art galleries, and Victorian mansions that Sag Harbor is famous for. The area has an expansive history as a 19th-century whaling hub, and the lovely property pays homage to that past with many decorative details, including the paintings of scrimshaw boats on the tiles around the sitting room fireplace and the resort’s logo itself—a take on a nautical signal flag.
Choose among the 67 village-facing or harborfacing rooms, each with a private outdoor sitting area, or opt for one of the family (and dog-friendly) suites. For some modern activities in a property so dedicated to honoring tradition, take a dip in the heated saltwater pool complete with cabanas or get an early morning workout in the fitness center.
Enjoy stunning sunsets during cocktail hour while relaxing in a rocking chair on the front porch.
Enjoy stunning sunset vistas over the cove during cocktail hour while relaxing in a rocking chair on the front porch or around the fire pit on the lawn. Then head to the second floor to dine at The Restaurant, beloved by locals and hotel guests for its fresh catch-of-the-day entrees, seasonal produce exclusively sourced from Long Island farms, and select East End wine vintages. Can’t-miss dishes include the Seafood Plateau (a delicious tower of oysters, shrimp, jonah crab claws, and accoutrements), the pan-seared local halibut, and the house-made three-cheese mac ’n’ cheese with lobster. After dinner on Fridays and Saturdays, go for a nightcap (and live music) in the lounge on the first floor.
If you want to venture off property, the Baron’s Cove team is happy to set up an outing. You can book a day trip to a local winery—Macari vineyards in Mattituck and Wölffer Estate Vineyard in Sagaponack are two standouts.
Seasonal rates for Baron’s Cove run from $250/night from March through September; the property is closed in the offseason.
Related: The Inn at Hastings Park Is a Historic Hideaway in Massachusetts
