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The Pridwin Hotel & Cottages

Stay Dates & Guests

A Bedroom With A Large Window
A House With A Tree In The Front
A Man And Woman Walking Down A Sidewalk

Rooms & Cottages

At the Pridwin

The Pridwin offers true Shelter Island luxury. Guest rooms in our historic hotel feature nautical touches, reflecting its perch above Crescent Beach. For more space and privacy, our Cottages sport private decks, living areas, and gas fireplaces.

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A Bed With A Bench In A Room With A Window
A Close-up Of A White Shirt With Black Text
A Bathroom With A Mirror And Sink
Bicycles Parked On A Sidewalk

Hillside Room

Equal parts cozy and classic, our sunny south-facing Hillside Rooms feature one King bed and views of the greenery and cottages nestled around the Pridwin grounds.
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A Bedroom With A Bed And A Chair
A Bathroom With A Large Mirror
A Bedroom With A Bed And A Television
A Bathroom With A Sink And A Mirror

Waterview Room

Our Waterview Rooms feature one plush King-size bed and breathtaking views of Crescent Beach. Take in a sunset over Long Island Sound—all from the comfort of your guestroom.
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A Bedroom With A Bed And A Tv
A Room With A Bed And A Tv
A Lamp And A Bed
A Bed In A Room
A Bathroom With A Mirror And Sink
A Drawing On A Board
Bicycles Parked On A Sidewalk
A Pool With Umbrellas And Chairs

Corner Preferred Room

Spacious and filled with natural light, our Corner Preferred Rooms feature windows on two sides of the guest room, enabling gorgeous water views of Crescent Beach and Long Island sound.
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A Bedroom With A Bed And A Chair
A Bed With A Lamp And A Bed With A Flower On It
A Room With A Door And A Lamp And A Deck With Trees
A Bed With White Sheets And Pillows
A Bathroom With A Sink And A Mirror
A Bedroom With A Bed And Chairs
A Tree Next To A Body Of Water
Bicycles Parked On A Sidewalk

Terrace Room

Located on the ground floor of the hotel, our spacious Terrace rooms feature an outdoor deck with breathtaking views of Crescent Beach.
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A House With A Tree In The Front
A Room With A Table And Chairs
A Bedroom With A Bed And A Tv
A Living Room With A Fireplace

Larch Cottage

Each Larch Cottage features a bedroom with a king-size bed, and a separate living room with a full-size sleeper sofa.
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A White House With A Green Door
A Living Room With A Fireplace
A Kitchen With A Couch And A Table
A Living Room With A Fireplace
A Deck With Chairs And A Table
A Bathroom With A Mirror And Sink
A Tree With Pink Flowers Next To A Body Of Water
Bicycles Parked On A Sidewalk

Birch Cottage

Quaint and well-appointed, our Birch Cottages offer private pet-friendly studio-style accommodations.
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A Living Room With A Fireplace
A Person Sitting At A Table
A Bed In A Room
A Deck With Chairs And Tables On It By A Body Of Water

Hickory Cottage

Our Hickory Cottages offer private studio-style accommodations with excellent water views overlooking Crescent Beach.
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A Living Room With A Fireplace
A Bathroom With A Mirror And Sink
A Bed In A Bedroom
A Deck With Chairs And Trees By A Body Of Water

Red Oak Cottage

Our Red Oak Cottages combine the beauty of water views with the convenience and privacy of separate living rooms.
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A House With A Small Patio
A Bed With White Sheets
A Living Room With A Couch And A Table
A Living Room With A Couch And A Table
A Bed In A Room
A Bathroom With A Shower Unit And Toilet
A Deck With Chairs And A House In The Background
Bicycles Parked On A Sidewalk

White Oak Cottage

Our White Oak cottages feature living rooms with double-height ceilings and separate bedrooms.
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A Kitchen With A Shelf With Flags
A Living Room With A Couch And A Table
A Bed With A Lamp And A Lamp On The Side
A Living Room With A Fireplace
A Green Couch With Pillows
A Bathroom With A Large Mirror
A Brown Bag On A Wall
Bicycles Parked On A Sidewalk
A Fire Pit With Chairs Around It

Caroline Cottage

Private and secluded, The Caroline Cottage offers house-style accommodations and views overlooking a wooded grove of trees.
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A Living Room With A Couch And A Coffee Table
A Table With Chairs And A Lamp
A Living Room With A Green Chair
A Living Room With A Couch And Chairs
A Room With A Table And A Vase With Flowers And Flags
A Bed With A White Bed Spread
A Bedroom With Two Beds
Bicycles Parked On A Sidewalk

Fraser Cottage

Nestled amongst a wooded grove of trees, the Fraser Cottage offers private house-style accommodations.
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Included in Your Stay

A Fire Pit With A Flame
Guest Activities
Friday, May 9, 2025
6:00 PM - 9:00 PM

S’mores on the Lawn

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Bicycles Parked On A Sidewalk
Guest Activities
Saturday, May 10, 2025
7:00 AM - 8:00 PM

Guest Bicycles

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A Person Holding A Tennis Racket
Guest Activities
Saturday, May 10, 2025
7:00 AM - 8:00 PM

Tennis & Pickleball

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A Person Standing On A Lawn Near A Body Of Water
Guest Activities
Saturday, May 10, 2025
8:00 AM - 8:00 PM

Cornhole

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A Cart With Baseball Bats And Balls
Guest Activities
Saturday, May 10, 2025
8:00 AM - 8:00 PM

Croquet

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A Group Of Flowers
Guest Activities
Sunday, May 11, 2025
9:00 AM - 2:00 PM

Mother’s Day Card Crafts at The Pridwin

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A Pot Of Flowers
Guest Activities
Sunday, May 11, 2025
2:00 PM - 4:00 PM

Flower Cutting at The Pridwin

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A Group Of Chickens In A Fenced In Yard
Guest Activities
Sunday, May 18, 2025
10:00 AM - 11:00 PM

Chicken Class with Chef Todd

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A Woman Sitting On A Dock
Guest Activities
Sunday, May 18, 2025
8:00 AM - 9:00 AM

Rise and Revive: Dynamic Movement Stretch Class

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A Man In A Canoe On A Lake
Guest Activities
Friday, May 23, 2025
10:00 AM - 8:00 PM

Kayaks & SUP

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A Silhouette Of A Boy Fishing
Guest Activities
Friday, May 23, 2025
8:00 AM - 8:00 PM

Fishing

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A Person Doing A Yoga Pose
Guest Activities
Monday, May 26, 2025
8:00 AM - 8:00 PM

Yoga on the Lawn

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A Carrot On A Grill
Guest Activities
Saturday, June 14, 2025
1:00 PM - 2:00 PM

Culinary Gardening

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Hands On A Keyboard
Guest Activities
Monday, June 16, 2025
8:00 AM - 8:00 PM

Mahjong Mondays

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A Group Of Kitchen Utensils
Guest Activities
Monday, June 16, 2025
1:00 PM - 3:00 PM

Art in the Grove

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A Group Of People Sitting On The Ground Watching A Television
Guest Activities
Monday, June 16, 2025
8:30 PM - 10:00 PM

Monday Night Movie in the Grove

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A Pizza On A Grill
Guest Activities
Tuesday, June 17, 2025
10:00 AM - 11:00 PM

Chefs in Training with Chef Todd

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A Group Of Shells
Guest Activities
Thursday, June 19, 2025
10:00 AM - 11:00 AM

Shell Hunt & Craft

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Email [email protected] Call (844) 200-5001

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