Tranquility & Tradition since 1927
Discover The Pridwin Hotel and Cottages, a historic beach resort that has welcomed guests on Shelter Island for nearly 100 years. After a top-to-bottom 2022 renovation, The Pridwin is now a tradition restored.
Mother’s Day Weekend
Mother’s Day Weekend
waterfront welcome
timeless tradition
Discover The Pridwin
A timeless Shelter Island classic.
Luxurious amenities and waterfront views intertwine at this incredible Shelter Island property, located between the North and South Forks of the Hamptons. Unwind in elegant rooms or private cottages, rejuvenate at The Pridwin Spa, and savor cuisine with stunning water views at The Terrace at The Pridwin.
Rooms & Cottages
The Pridwin offers 33 well-appointed guest rooms and 16 private cottages set atop nearly 10 scenic acres overlooking Crescent Beach.
Guest Rooms
Inside our historic hotel, each guest room features nautical accents throughout—a nod to the Pridwin’s location perched on a rise overlooking Crescent Beach.
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Private Cottages
The Pridwin Cottages offer a spacious and private stay, complete with private decks, living areas and gas fireplaces.
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The Pridwin Hotel & Cottages
During Your Stay
The Pridwin presents a host of experiences to enjoy—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™. Plus, you’ll love thoughtful touches like a deluxe Continental Breakfast each morning of your stay, rounding out the ultimate Hamptons escape on Long Island’s East End.
Summer at The Pridwin is pure Shelter Island magic. Guests can soak up the sun on a private beach, take a refreshing dip in the waterview pool, or explore the island by kayak, paddleboard, or bicycle. Lawn games like cornhole and croquet add to the nostalgic charm, while children’s programs like Chicken Class and Monday Movie Nights keep younger guests happily entertained. Evenings bring live music, sunset cocktails from The Crescent Bar, and candlelit dinners on The Terrace, the Pridwin’s water-view restaurant—where seasonal, local ingredients shine.
As summer fades, The Pridwin becomes a cozy coastal retreat ideal for couples, friends, or solo travelers. Guests can play tennis or try pickleball on the courts, hike through nearby Mashomack Preserve, or stroll along the shoreline under golden foliage. After a day outdoors, sip cider fireside or enjoy seasonal, elevated fare at the on-site restaurant. With charming cottages and a peaceful pace, fall at The Pridwin is all about savoring Shelter Island at its most serene.
Pridwin Packages
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.
Grand Reopening: Mother’s Day Weekend
The Pridwin will reopen on Friday, May 9—and we’ve packed the weekend with activities, excursions, and delicious dining she’ll love.
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.
Wednesday Night BBQ Package
Stay overnight for a legendary Pridwin Wednesday Night BBQ and enjoy a great rate, BBQ tickets, and two complimentary cocktails.
Sunset Cruise Getaway
Escape with a beautiful sunset cruise on our boat, Fred's Folly—paired with rosé and lobster rolls!
Hook to Cook at The Pridwin
Join us on Shelter Island this fall for a whirlwind weekend featuring freshly-caught fish and friendly competition.
Dinner on the Terrace
Join us for dinner at The Pridwin while taking in the beautiful views of Crescent Beach.
Pridwin Pup Retreat
Bring your four-legged family member on your Pridwin getaway and enjoy deluxe dog-friendly accommodations in a private Birch Cottage.
The Benjamin: $100 Resort Credit
Stay with us in Cape May or The East End and enjoy a $100 resort credit—with the freedom to choose how to spend it.
AAA & AARP Member Rate
Take advantage of our AAA & AARP savings and enjoy discounts off our daily rates.
Dining at The Pridwin
The Terrace & Crescent Bar
Take your seat on The Terrace, the Pridwin's magnificent water-view restaurant and bar. Indoor seating spills out to the deck, where each seat commands spectacular views over Crescent Beach. True to Pridwin tradition, this reimagined restaurant serves classic Long Island food and drink—with a focus on high-quality ingredients sourced from local farms and makers.
Upcoming Events at The Pridwin
Guest Activities
Special Events
Dinner Series
Saturday, May 10, 2025
6:00 PM - 8:00 PM
Mother’s Day Weekend Dinner with Macari Vineyards
Live Music
Guest Activities
Guest Activities
Guest Activities
Guest Activities
Live Music
Special Events
Guest Activities
Guest Activities
Live Music
Live Music
Guest Activities
Guest Activities
Live Music
Guest Activities
Guest Activities
Live Music
Live Music
Guest Activities
Live Music
Special Events
Live Music
Live Music
Live Music
Live Music
Special Events
Dinner Series
Guest Activities
Guest Activities
Guest Activities
Guest Activities
Special Events
Guest Activities
Guest Activities
Special Events
Dinner Series
Dinner Series
Special Events
Gather at The Pridwin
The Pridwin Hotel and Cottages offers an ideal setting for executive meetings, group retreats, and unforgettable weddings.
Weddings
The Pridwin provides a stunning venue your wedding and reception. From a custom dining menu to on-site coordination, our team will work personally with you to achieve your vision.
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Meetings
The Pridwin's beautiful campus fosters the perfect environment for organic and authentic team-building opportunities.
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Our Stories
Where Time Has Stood Still
Named after the shield (“Prid’win”) of the legendary Celtic hero, King Arthur, the Pridwin Hotel was built from 1924 to 1926 by an English concern named the Queens Company Ltd.
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A Tradition Returns
“A friend approached me while I was out to dinner one night,” says Glenn Petry, co-owner and chief nostalgia officer of The Pridwin. “She told me: You have to bring back the cookouts..."
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