As a guest of The Pridwin, nearly ten waterfront acres become your playground. Enjoy the pool and private beach, with on property dining and al fresco moments by the water. Court sports and two game rooms offer time to play, along with a sprawling lawn for croquet, cornhole, and classic outdoor games.
Set out on an unforgettable adventure aboard Fred's Folly, our classic Pridwin boat, for a cruise around Shelter Island. Take in the charm of Dering Harbor, with its historic homes, bobbing sailboats, and timeless coastal beauty, all from the best seat in the house-on the water. Whether you're sipping a cool drink, snapping photos, or simply soaking up the sea breeze, a cruise on Fred's Folly is the perfect way to experience the island's maritime magic.
Boat Cruises are available for an additional fee. See the Front Desk to reserve.
Every Pridwin Hotel and Cottage getaway features complimentary guest activities hosted at our beautiful hotel. We invite you to browse our selection below to plan your vacation.
View Full CalendarInside, The Pridwin feels like a whimsical home. Settle in fireside. Restore at the full service spa and fitness center.
Cycle quiet roads, kayak along the shoreline, or set out on sunset cruises. Take a Moke to Mashomack Preserve, then explore its trails on foot. Shelter Island Village remains beautifully untouched by time, offering charming shops, relaxed dining, and a slower pace to discover.
Explore Shelter Island's expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination. Our fleet of kayaks and stand up paddle boards are ready for adventure, and the calm bay current surrounding Shelter Island make taking to the water a breeze. Our kayaks and paddle boards are available seasonally for guest use and are first come, first serve.
Below, we list a few of our favorite places to paddle. Be sure to consider tides and currents when planning your route.
Located by the resort's ground-floor Lobby, Edie's is your one-stop shop for everything Camp Pridwin. You'll find an assortment of sundries here-anything from Sun Bum sunscreen to our very own Beach Plum Farm bath products-as well as a collection of limited-edition Pridwin branded merchandise, such as beautiful branded canvas totes from Shore Bags.
Edie's is lovingly named in honor of Edie Petry, mother of Glenn and Gregg Petry.
Practice your backhand or simply get back into the swing of things on our court. Rackets and tennis balls are available for complimentary guest use from the Front Desk. Please contact Concierge to reserve the court for play.
Kids and kids-at-heart will love The Pridwin's amenities and wide open space, as well as a host of rousing activities from sunup to sundown-all set amongst the classic American charm of our Shelter Island resort.
The Game Room at The Pridwin offers a lively space for guests to relax, connect, and enjoy a little friendly competition in a classic atmosphere.
From rainy-day card games to late-night Monopoly tournaments, the Nook game room has everything needed for hours of fun any time of year.
Sitting on nearly ten acres of wooded grounds lining Crescent Beach, the Pridwin's bucolic campus makes it the perfect hub for classic outdoor fun.
Take a dip in our beautiful water-view pool, perched with a breathtaking view over Crescent Beach. Pool Attendants will be on-hand with complimentary towels, as well as menus for cocktails and light bites.
Plus, when the tide is right, we'll be glad to set you up with chairs, towels, and umbrellas on The Pridwin's private beach, directly in front of the hotel.
Whether traveling as a family, escaping as a couple, or gathering with friends, each experience unfolds with ease.
During your stay, our knowledgeable Concierge is your one-stop resource for all things Shelter Island. We'll gladly assist you with dining reservations, spa treatments, and anything else you need to make your vacation even more special.
