Nestled between the Hamptons at the East End of Long Island, Shelter Island feels like a world away. Accessible only by ferry, the journey itself feels like the first stamp in a passport to somewherenew—and an invitation to a slower, more meaningful way of life. Here, time moves differently. Days unfold with intention, shaped more by tides and tradition than by clocks or calendars. And at the heart of it all is The Pridwin—your passport to the magic of a classic American summer that feels untouched by time.
Daily activities like kayaking, pickleball, and cornhole accent The Pridwin guest experience.
Complimentary continental breakfast features made-to-order omelettes and fresh pastries.
The Pridwin is your passport to relax together as a family, playing cornhole on the lawn before a dip in the pool. There’s a host of experiences to enjoy here—from kayaking and paddle boarding, to pickle ball, croquet, and tennis. Hike scenic Mashomack Preserve, and explore the island at your leisure by bike or Moke™.
The Pridwin is your passport to relax together as a family, playing corn hole on the lawn before a dip in the pool.
Breakfast each morning, s’mores each evening, and family adventures in between.
The Pridwin is your passport to relax together as a family, playing cornhole on the lawn before a dip in the pool. There’s a host of experiences to enjoy here—from kayaking and paddle boarding, to pickle ball, croquet, and tennis. Hike scenic Mashomack Preserve, and explore the island at your leisure by bike or Moke™.
Packages
Wednesday Night BBQ Package
Join us for a beloved Pridwin BBQ on the lawn, featuring an elevated all-you-can eat cookout menu.
Summer Tastes: Midweek Dinner Offer
A midweek escape at The Pridwin, accented deliciously by dinner for two—on us!
Magic Hour Boat Cruise Package
Set out for a cruise on our boat, Fred’s Folly, with a bottle of rosé and two Lobster Rolls.
What a Difference a Day Makes
On Shelter Island, an extra day makes all the difference. Extend your Pridwin stay a little longer and save.
Classic American Summer at The Pridwin
There’s a certain kind of summer that lives only in memory. At The Pridwin, that summer still exists.
Girls’ Getaway at Macari Vineyards
Grab your crew for a getaway to The Pridwin, where you’ll enjoy spa treatments and a trip to Macari Vineyards.
AAA & AARP Member Rate
Take advantage of our AAA & AARP savings and enjoy discounts off our daily rates.
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