The Pridwin Hotel & Cottages

Stay Dates & Guests

People Playing In The Water

Classic American Summer at The Pridwin

Available Summer 2025

The Pridwin Hotel and Cottages

There’s a certain kind of summer that lives only in memory—crisp linen sheets after sun-drenched afternoons, the scent of salt air carried on a bay breeze, Adirondack chairs on lush green grass besides blooming hydrangeas. At The Pridwin, that summer still exists.

There’s a certain kind of summer that lives only in memory—crisp linen sheets after sun-drenched afternoons, the scent of salt air carried on a bay breeze, Adirondack chairs on lush green grass besides blooming hydrangeas. At The Pridwin, that summer still exists.

Perched on the gentle shores of Shelter Island since 1927, The Pridwin is a season unto itself. Mornings begin with coffee on lawn and the distant hum of sailboats setting off. Afternoons stretch into golden hours by the pool, or a lazy kayak paddle on the water. Evenings bring BBQs on the lawn, live music on porch, and the soft flicker of lanterns as the sunset slips into night.

Included in your Summer Getaway

A Man And Woman Holding A Couple Of Children On A Beach
It’s not just a getaway—it’s a return.

Summer Fun at The Pridwin

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

S’mores on the Lawn

A Group Of People Holding Glasses
Special Events
Friday, May 9, 2025
2:00 PM - 4:00 PM

Champagne Toast on the Lawn

A Person Pouring A Glass Of Wine
Dinner Series
Saturday, May 10, 2025
6:00 PM - 8:00 PM

Mother’s Day Weekend Dinner with Macari Vineyards

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

Croquet

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

Cornhole

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

Tennis & Pickleball

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

Guest Bicycles

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

Flower Cutting at The Pridwin

A Dining Table With A Set Of Chairs And A Plant On It
Special Events
Sunday, May 11, 2025
10:30 AM - 2:30 PM

Mother’s Day Brunch at The Pridwin

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

Mother’s Day Card Crafts at The Pridwin

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

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

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

Fishing

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

Kayaks & SUP

A Plate Of Sushi
Special Events
Monday, May 26, 2025
5:00 PM - 9:00 PM

Memorial Day BBQ

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

Yoga on the Lawn

A Group Of Tables And Chairs Next To A Body Of Water
Special Events
Wednesday, June 11, 2025
5:00 PM - 9:00 PM

Wednesday Night BBQs

A Hand Holding A Plate With Food
Dinner Series
Thursday, June 12, 2025
6:00 PM - 8:00 PM

Summer Truffle Dinner

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

Culinary Gardening

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

Mahjong Mondays

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

Art in the Grove

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

A Group Of White Mushrooms
Special Events
Tuesday, June 17, 2025
4:00 PM - 6:00 PM

Oysters & Bubbles

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

Chefs in Training with Chef Todd

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

Shell Hunt & Craft

Fireworks In The Sky
Special Events
Saturday, July 12, 2025
9:00 PM - 9:30 AM

Shelter Island Fireworks Show

A Group Of Tables With White Tables And White Chairs
Dinner Series
Thursday, August 21, 2025
6:00 PM - 8:00 PM

Summer Harvest Dinner

A Table With Food And Drinks On It By A Tree And A Body Of Water
Dinner Series
Monday, September 1, 2025
5:30 PM - 9:00 PM

Labor Day BBQ

A Group Of People Sitting At A Table With Food And Drinks
Special Events
Saturday, October 11, 2025
12:00 PM - 6:00 PM

Fall Fest at The Pridwin

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