The Pridwin Hotel and Cottages

Stay Dates & Guests

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A Table With Food And Drinks On It
Bicycles Parked On A Sidewalk

Resort Amenities

Thoughtful Conveniences & Daily Adventures

Unwind, play, and explore at The Pridwin with beachside lounging, live music, spa treatments, lawn games, kayaking, and endless ways to enjoy Shelter Island.

On-Property Amenities

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Continental Breakfast

Each morning at The Pridwin begins with a complimentary continental breakfast featuring an omelette station, fresh pastries, seasonal fruit, cereals, yogurt, coffee, and seasonal accompaniments. Enjoy a relaxed start to your day in the bright, welcoming dining space, or take your breakfast outdoors for a peaceful moment overlooking Crescent Beach.. Click here to learn more.
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A Bed In A Room

Signature Bedding

Drift into comfort with The Pridwin's signature bedding, designed to ensure a restful night's sleep. With plush pillows, crisp all-cotton linens, and cozy duvets, you'll wake up feeling refreshed and ready for another day of island adventures or blissful relaxation by the water.

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Room Service

Savor the flavors of The Pridwin from the comfort of your room with our convenient room service. Whether it's breakfast in bed, afternoon snacks, or dinner on your private balcony, enjoy chef-prepared meals delivered right to your door for a truly indulgent experience.

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On-Property Dining

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.

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The Pridwin Spa

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.

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Fitness Center

Keep your workout routine going at The Pridwin's Fitness Center, equipped with modern cardio machines, 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.

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A Pool With Umbrellas And Chairs

Pool & Beach Service

Soak up the sun with ease thanks to The Pridwin's pool and beach service. Our team handles towels, chairs, and refreshing drinks, leaving you free to lounge by the pool or on Crescent Beach with nothing to think about except relaxing by the water.

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Guest Bicycles

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.

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Guest Activities

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.

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Tennis & Pickleball Court

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.

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Kayaks & Paddle Boards

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.

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Fishing

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.

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Lawn Games

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.

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Game Room

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.

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A Living Room With A Wood Floor

The Nook

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.

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Edie's Gift Shop

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.

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The Grove

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.

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Live Music

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.

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Complimentary Parking

Enjoy hassle-free travel with complimentary on-site parking. 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.

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Complimentary WiFi

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.

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A Person On A Small Car
Enhance Your Stay

Moke™ Rentals

The Pridwin is proud to partner with Moke to offer our guests a fleet of fun, open-air vehicles available for rent during their stay. These street-legal, low-speed electric cars are an ideal way to explore Shelter Island at your own pace-cruise to local beaches, visit charming shops, or simply enjoy the breeze as you take in the island's scenic beauty. With their retro design and eco-friendly build, Moke vehicles combine style, convenience, and sustainability, turning every drive into a memorable part of your vacation experience.

Moke rentals are available for an additional fee. Vehicles are available on a first-come, first-serve basis. Please see the Front Desk to reserve.

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A Group Of People On A Boat
A Few People Working On A Boat
Enhance Your Stay

Fred’s Folly Boat Cruises

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.

Request Information

For all inquiries for meeting rooms, weddings or events over 10 persons, please fill out the form below.
Wedding | Request For Proposal

Wedding | Request For Proposal