Relaxed East End days that feel both unhurried and quietly full. Complimentary experiences, from time on the water to sunset moments on the lawn, are thoughtfully woven in so you can simply arrive and enjoy.
When the tide is low, The Pridwin’s private beach is the perfect spot to soak up the sun. Our team handles towels, chairs, and umbrellas, leaving you free to lounge by the water and take in the gentle rhythm of the waves. Stretch out with a good book, stroll along the shoreline, or simply unwind as the sea breeze drifts by—every detail is thoughtfully arranged so you can fully relax and enjoy the moment. Click here to learn more.
The Pridwin’s heated pool sets the scene for an easy, sun-filled day by the water. Poolside attendants provide chairs, towels, and umbrellas, so you can settle in without a second thought. Enjoy a relaxed lunch from the full poolside menu, or sip a signature cocktail from the Osprey Nest, our pool bar. Whether you’re taking a refreshing dip or unwinding in the shade, every detail is in place for a carefree afternoon. Click here to learn more.
Drift into comfort with The Pridwin's signature bedding, designed to ensure a restful night's sleep. With signature Pridwin luxury mattresses, pillows, all-cotton linens, and plush bathrobes, you'll wake up feeling refreshed and ready for another day of island adventures or blissful relaxation by the water.
Thoughtfully appointed in-room amenities add ease to your stay, including a Nespresso machine and convenient beverage chiller. Start your morning with a curated selection of Nespresso blends, along with decaffeinated and herbal tea options to suit your preference. Your under-counter beverage chiller keeps refreshments perfectly cool and within reach throughout your visit. Additional touches such as an in-room safe, HDTV, telephone, and individual climate control ensure a comfortable stay from start to finish.
Savor the flavors of The Pridwin from the comfort of your room with our convenient room service. Whether it's a light lunch before you head out for the afternoon, or a multi-course dinner on your cottage's private deck, enjoy chef-prepared meals delivered right to your door for a truly indulgent experience.
Savor coastal-inspired cuisine at The Pridwin's restaurant, The Terrace, where fresh seafood and seasonal ingredients meet stunning water views. The iconic Crescent Bar serves a range of classic cocktails and new twists, while the Osprey Nest bar keeps spirits up poolside. From casual bites to elegant dinners, every meal at The Pridwin captures the relaxed charm of Shelter Island dining.
Keep your workout routine going at The Pridwin's Fitness Center, equipped with Pecor and Peloton equipment, free weights, and stretching areas. Whether you're squeezing in a quick session or enjoying a full workout, staying active during your stay is simple and convenient with this well-appointed space.
Escape to The Pridwin Spa, a serene space designed for relaxation and renewal. Treat yourself to a soothing massage, revitalizing facial, or custom treatment crafted by expert therapists. Just steps from the water, it's a peaceful retreat where the natural beauty of Shelter Island enhances every visit.
Unwind in The Pridwin's serene Sauna and Steam Room, where warmth and tranquility melt away tension. These calming spaces provide the perfect retreat after a day of exploration, soothing muscles and quieting the mind. Refresh your senses and embrace deep relaxation in this restorative wellness haven by the water.
Pedal your way around Shelter Island with complimentary guest bicycles, perfect for exploring the charming neighborhoods, quiet wooded paths, and scenic coastal roads. Whether you're on a leisurely ride to Crescent Beach or adventuring to a local landmark, it's a breezy, fun way to see the island up close.
Make the most of your getaway with The Pridwin's curated calendar of guest activities. From nature walks and art classes to lawn games and evening s'mores by the fire, there's always something fun to do-perfect for guests of all ages looking to create lasting Shelter Island memories.
Stay active and have some fun with a friendly game on The Pridwin's tennis and pickleball court. Whether you're an experienced player or just learning, this all-ages activity is a lively way to spend time outdoors while soaking up Shelter Island's refreshing coastal air and sunshine.
Hit the water with complimentary kayaks and paddle boards, offering a fun and adventurous way to experience Shelter Island. Paddle at your own pace, explore the coastline, or simply float under the sun-it's an easy and memorable way to enjoy Shelter Island's natural beauty from the water.
Whether you're a seasoned angler or simply casting for fun, fishing on Shelter Island is a rewarding way to connect with nature. Drop a line along the shore or from the dock and enjoy the quiet, timeless joy of fishing against a picturesque coastal backdrop.
Step onto The Pridwin's lush green lawn for classic outdoor games like cornhole, bocce, and croquet. It's the perfect way to spend an afternoon with family or friends, enjoying friendly competition and the relaxed, open-air charm of Shelter Island's beautiful natural surroundings.
The Game Room is your go-to spot for laid-back fun, featuring ping pong, classic board games, and plenty of space to relax. It's the perfect place to enjoy a rainy afternoon, gather with friends for a friendly match, or let the kids unwind between island adventures.
Settle in at The Nook, a cozy space designed for leisurely indoor fun. Play a round of chess, dive into classic board games, or enjoy an afternoon of quiet competition. It's a welcoming gathering spot perfect for unplugging, unwinding, and sharing laughter with family or friends.
Relax and unwind at The Grove, a natural outdoor amphitheater gathering space framed by a canopy of trees. Whether you're enjoying cocktails at sunset, savoring s'mores by the fire, catching a family movie on the big screen, or relaxing under twinkling lights, this inviting gathering space captures the easygoing essence of Shelter Island living at its very best.
Take a little piece of The Pridwin home with you from Edie's Gift Shop. Browse a curated collection of souvenirs, local treasures, and travel essentials-perfect for picking up beach gear, finding a thoughtful gift, or selecting the ideal keepsake to remember your stay.
Settle into an unforgettable Shelter Island evening with live music at The Pridwin. From acoustic performances to lively sets, enjoy an evening soundtrack that pairs perfectly with sunsets, cocktails, and the kind of easy, unhurried moments that make a getaway truly memorable.
Enjoy hassle-free travel with complimentary on-site valet and self-parking options. Whether you're here for a weekend escape or a longer stay, convenient parking ensures easy arrivals and departures, leaving you more time to relax and explore the island.
Stay as connected-or as unplugged-as you like with complimentary high-speed WiFi throughout The Pridwin. Whether you're sharing vacation photos, streaming your favorite show, or catching up on emails, reliable internet access makes it easy to balance work, play, and relaxation during your stay.
Set out on an unforgettable adventure aboard Fred's Folly, our classic Pridwin boat, for an hour-long cruise around Shelter Island. Glide past the picturesque shoreline and enjoy stunning views as you make your way through the sparkling waters of the Peconic. 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. Vehicles are available on a first-come, first-serve basis. Please see the Front Desk to reserve.
From chilled champagne upon arrival, to custom cheese and charcuterie boards, to flowers on your nightstand-our talented Pridwin team is at your service to make your stay that much more magical. We will be glad to accommodate special requests for personalized amenities throughout your stay.
Our Reservations Team is ready to assist you with planning the perfect getaway to Shelter Island.
