Imagine stepping foot into the chicest summer camp you’ve ever laid eyes on, which doubles as a storied resort on Shelter Island — that’s what pulling up to The Pridwin feels like (minus the actual camp part). Campfires and 10 acres of rolling, camp-like grounds, yes, but actual camp counselors? Not so much.
While the young squad of staffers who cheerily chauffeur you to your cottage in a golf cart sort of fit the bill, The Pridwin is like no other seaside sanctuary in Shelter Island, or on the East Coast for that matter. It’s truly unique in its style and ethos, with a history rooted in hospitality.
Dating back to 1927, the Grand Dame resort is still the largest property on the 27-mile-long island. But after a fateful partnership between current owners the Petry family and Cape Resorts (who also manage boutique hotels Baron’s Cove in Sag Harbor and Congress Hall in Cape May, NJ), The Pridwin finally reopened last year. Just a bit bigger and shinier after a two-year, top-to-bottom renovation.
The refresh saw the addition of a restaurant and spa. The rooms and cottages have been modernized but Colleen Bashaw, the hotel’s designer, took great pride in keeping the original structure and bones the same, which meant leaving the famous white facade and those iconic hunter-green window encasements.
As for the accommodations, the main hotel houses 33 guest rooms awash in coastal colors and outfitted with nautical touches like antique sea charts and framed boat replicas. Then there are the 16 private cottages, each with its own gas fireplace, kitchenette, and expansive veranda. Even the upholstery is nostalgic and playful: chairs and pillows in bold botanical prints intermix with crisp white bed linens and decorative canoe oars, creating a very inspired place of shelter.
A proper evening at The Pridwin begins at their horseshoe-shaped, striped-awning-clad Crescent Bar, which serves as the social hub for the resort. They offer classic cocktails (think Hemingway Daiquiris and Vespers) as well as more creative libations.
Since breathtaking, waterfront views are the heart and soul of The Pridwin, we would expect nothing less from their restaurant, The Terrace, which is perched above Crescent Beach and offers the best vantage point with sweeping views of the Peconic Bay. Here, you’ll marvel at Shelter Island’s unparalleled sunsets, before diving into Long Island-style seafood dishes like Fritto Misto with lemon caper tartar sauce, crab cakes with mango slaw, and grilled striped bass with stone fruit.
Live music is also a nightly occurrence, with a rotating roster of talent ranging from pianists to rock cover bands and no morning is complete without a Pridwin doughnut stack. The pile of plain, cinnamon-sugar, and confectioner’s sugar-dusted doughnuts is a nod to the hotel’s glory days when they were served the same way.
Although recreational activities and water sports abound, you’ll want to make time for a pampering treatment at The Pridwin Spa, where you can relax with a massage or a seaweed facial. For the yogis, practice your tree pose surrounded by nature, every Monday, Wednesday, and Friday at 8 a.m. on the great lawn.
Top Takeaways
Location: Shelter Island, New York
Star-Rating: Four-Star
The Vibe: A classic American resort hotel on the shores of Shelter Island that evokes a bygone era.
Our Favorite Thing About the Hotel? They have a private dock and boat to take you to their sister hotel Baron’s Cove in Sag Harbor if feel the need to go off the island for the day. Go shopping in Sag, have lunch at Lulu Kitchen and Bar, then a drink at the bar at Baron’s before heading back to Shelter.
Food + Drink: The Pool Bar; Crescent Bar; The Terrace Restaurant
Any Neighborhood Recs? We love French-Italian restaurant Leon 1909 for locally sourced fare prepared over a wood hearth, organic market Marie Eiffel for beach sandwiches and snacks, The Flying Goat for lunch or dinner, Sunset Beach for sunset spritzes and a lights-out Linguine Vongole, The Ram’s Head Inn for Monday night trivia and Stars for gourmet coffee and pastries.
Amenities: A private beach and swimming pool; The Pridwin Spa; fitness center and tennis court; complimentary yoga classes; The Nook game room; free valet parking and minibar items; the use of bikes, paddleboards, kayaks, fishing poles; motorized water sport rentals.
What’s Nearby? Crescent Beach; Menhadden Lane Beach; Mashomack Nature Preserve; The Shelter Island Country Club with a nine-hole public golf course.
Rooms: 33 guest rooms and 16 private cottages.
Pricing: Rooms start at $329/night; cottage rates start at $1,000/night.
Closest Airport: The easiest way to access The Pridwin is by ferry service to Shelter Island from the North Fork via Greenport and the South Fork via Sag Harbor but the closest airports are East Hampton, Islip, Hartford, and White Plains.
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