Welcome Home—
Nestled in Shelter island Heights overlooking Dering Harbor, The Chequit Hotel has a long standing history within the community as a year round destination and events venue. Explore the signature experience with fine dining, special events and casual sophistication.
Natives to the island are regulars here at the hotel’s local Tavern, so whether you’re joining us for a Hamptons experience or just checking out the café, our doors are open to welcome you inn.
Dine With Us —
Indulge in the experience of coastal fine dining or casual Americana cuisine. Formal seating offers a delicious selection from the Chef’s menu featuring a coastal influence of flavor to savor. For a more local vibe, head downstairs to the Tavern for burgers and truffle fries. Bring your friends and enjoy the relaxing vibes of The Chequit with harbor views.
Dining Menu
Bar Menu
Order Online
The Cafe —
Welcome to Shelter Island’s newest café nestled in The Chequit Hotel - a haven for coffee lovers and seekers of serenity alike.
It’s not just a café, it’s a destination.
Try the Chef’s fresh pastries or gourmet coffee from Brooklyn Roasting Co. Matcha is also served with milk alternatives. Explore the grounds, enjoy the views and take a moment to unwind.
CLOSED for the season
Burger Night
Sundays
Sundays are better with burgers! Join us at The Chequit for Burger Night, where you can sink your teeth into a juicy, chef-crafted burger served with crispy fries — all for just $16. It’s the perfect way to wrap up the weekend: simple, satisfying, and best enjoyed with friends (and maybe a cold drink in hand).
Come hungry!
5 - 10pm
Bingo Night
Every Wednesday
Gather your friends, grab a cocktail, and get ready for a night of classic fun at The Chequit! Join us for Bingo Night, where laughter fills the air and every round brings a new chance to win prizes and bragging rights. Whether you’re a seasoned player or trying your luck for the first time, it’s the perfect way to unwind, connect, and enjoy an easygoing evening in the heart of Shelter Island.
Let’s play!
6pm
Get ready to savor the freshest flavors of the sea — one delicious bite at a time! Join us for Buck-a-Shuck at The Chequit, where oysters, shrimp, and clams are just $1 each. Perfect for a laid-back afternoon or a lively start to your evening, it’s a celebration of coastal tastes, good company, and unbeatable deals. Come sip, savor, and shellabrate with us!
Every Thursday
Buck-a-Shuck
Starting at 5pm
Prix Fixe Menu
Friday Nights
Join us for a fantastic Friday night special! Enjoy our prix fixe menu featuring exquisite dishes, all while savoring half-off bottles of wine from Peconic Bay Vineyards. Treat yourself to a night of culinary delights and fine wine at an unbeatable price. Reserve your table now and make your Friday truly special!
5 - 10pm
Weekend Brunch
Saturdays and Sundays
Ease into the weekend with a delicious brunch at The Chequit, served every Saturday and Sunday from 12–3PM. Sip, savor, and soak up the Shelter Island charm with chef-inspired dishes, refreshing cocktails, and the perfect laid-back vibe. Whether you’re fueling up for an afternoon adventure or lingering over mimosas with friends, brunch at The Chequit is always a good idea.
See you at the table!
12 - 3pm
Guest Rooms —
M A I N H O U S E R O O M S
Newly renovated with fine finishes throughout
King-size beds with fine Frette linens and towels
Luxe rain shower with Malin+Goetz bath amenities (suites offer claw-foot tubs)
Free, fast Wifi
Mini fridge & safe
Central AC & heat with remote
Sound-proofed windows with push-button blackout shades
TV for streaming
Walk to Dering Harbor Village, beach, tennis and North Ferry for easy, walkable access to Greenport.
eBike Rental
Dog Friendly
Private Event Space
Looking to host a private party or a special occasion? Our house is your house. Let’s plan a memorable event the guests are sure to celebrate years to come.
Follow our journey on instagram @thechequit
