The Pridwin Hotel & Cottages

Shelter Island’s refreshed retro retreat

Time seems to stand still on Shelter Island, an enclave tucked between Long Island’s North and South forks where New York’s elite have come to summer for a century at places like The Pridwin Hotel & Cottages. With such a storied history, it’s understandable that locals and longtime visitors would be anxious about the island’s largest hotel undergoing a two-year renovation. But when the property debuted its new look at a soft opening in 2022, the public breathed a collective sigh of relief.

Restored rather than renovated at the hands of New York-based management company Cape Resorts, The Pridwin’s stately exterior neatly matches historic photos of the 90-plus-year-old property while playful touches of nostalgia (vintage signage and wicker furniture) in public spaces are made modern with contemporary colors. In keeping with the boutique hotel’s storied past, the vibe here is summer camp meets vintage vacation, where your only obligations are deciding how to laze away sunny island days.

Our Inspector's Highlights
  • The Pridwin Hotel & Cottages’ prime address and elevated perch provide some of the best Peconic Bay views around. Its Shelter Island location also means it's much quieter than other Long Island enclaves, making it the perfect spot to get away from it all.
  • Those looking to venture further than The Pridwin’s grounds can take advantage of the boutique hotel’s bike program to explore nearby beaches and shops. You can also charter the property’s private boat for a fishing trip or to do some sightseeing around North Fork and Greenpoint.
  • The Shelter Island hotel’s refresh includes an updated farm-to-table menu at the aptly named Terrace restaurant. Savor sea-focused fare sourced from local producers and farmers paired with sea breezes and sundowners on the restaurant’s expansive (you guessed it) terrace.
  • Sprawled across seven and a half acres of beachfront property, The Pridwin rarely feels crowded, even when all 33 rooms and 16 private cottages are occupied.
  • When it comes to relaxation, there are seemingly endless ways to unwind here. Laze your day away on Crescent Beach or the shaded pool, enjoy a round of bocce or pickleball, head out on a kayak, savor nightly s’mores or check out the game room for some old-fashioned family fun.

The Look
  • Shelter Island’s overall aesthetic is much more laid-back beachy chic than cosmopolitan Montauk, a vibe The Pridwin Hotel & Cottages’ new look embraces with whimsical wallpaper and vintage touches like model ships and framed maps.
  • Rather than stick with the typical nautical palette of other New England seaside hotels, Pridwin designer Colleen Bradshaw opted for more contemporary colors like emerald, taffeta pink and white.
  • Richly patterned textiles from designers such as Pierre Frey and Lisa Fine bring a pop of color and playfulness to neutral-toned accommodations — think New York’s answer to Palm Beach’s Lilly Pulitzer dresses.
  • Though accommodations lean into the coastal whimsy vibe, bathrooms boast modern luxuries like brass fixtures, heated floors and, in most rooms and cottages, ocean views.
  • Even the Pridwin Spa embraces the luxury hotel’s playful adult summer camp aesthetic with bold Josef Frank wallpaper and framed vintage swimwear as artwork.
Fitness classes
House car
Meeting rooms
Outdoor pool
Pet friendly
Getting There
81 Shore Road, Shelter Island Heights, NY 11965
JFK (2 hr 10 min-2 hr 40 min)   HTO (45 min)   MTP (1 hr 15 min)  
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