Welcome Home
Since 1872, The Chequit has been a gathering place for travelers and locals alike. Set above Dering Harbor, our historic boutique hotel offers refined simplicity, coastal calm, and the kind of warm hospitality that has defined Shelter Island for generations.
From leisurely mornings at the café to evenings in the Chequit Restaurant, every moment here feels comfortably timeless.
Dine With Us
The Chequit Restaurant brings seasonal, Italian coastal flavors to the main level of our historic inn.
Our upstairs dining room has been reimagined as a private event space, perfect for celebrations, group dinners, and catered gatherings.
Dining Menu
Cocktails, Wine & Beer
The Heights Café
Welcome 2026 at the Heights Cafe located in The Chequit— a cozy, sun‑washed café designed for coffee lovers, pastry seekers, and anyone craving a quiet moment on Shelter Island.
It’s not just a stop; it’s a place to linger.
Try the Chef’s fresh pastries, enjoy Brooklyn Roasting Co. coffee, or relax with a matcha made just the way you like it. Explore the grounds, take in the views, and let yourself slow down.
Open7am–3pm
The Chequit Guest Rooms
Thoughtfully renovated and designed with comfort in mind, each room at The Chequit blends modern ease with timeless coastal charm.
Enjoy a king‑size bed dressed in luxurious Frette linens and towels, paired with fine finishes throughout the space. Refresh in a luxe rain shower with C.O. Bigelow bath amenities — and in our suites, unwind in a classic claw‑foot tub.
Your stay includes:
Fast, complimentary WiFi
Mini‑fridge and in‑room safe
Central heating & air conditioning with remote control
Sound‑proofed windows and blackout shades for restful sleep
Cable TV and streaming access
Step outside and you’re moments from Dering Harbor, the beach, tennis courts, and the North Ferry for easy access to Greenport.
For exploring the island, bike rentals are available on a first‑come, first‑served basis.
Private Event Space in our Garden Room
Looking to host a private party or a special occasion? Our house is your house. Let’s plan a memorable event for you and your guests that will be remembered for years to come.
Restaurant Gift Cards
Event Inquiry
Follow our journey on instagram @thechequit
Join The Chequit Club
