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

Bar Menu

Order Online

Food & Entertainment

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

Learn more

Weekend Brunch

12 - 3pm

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!

Daily Happy Hour

4 -6pm

Intimate Gatherings, Coastal Charm

At The Chequit, we believe the best celebrations are the ones that feel personal, effortless, and beautifully hosted. Our private event spaces — from the sun‑filled Garden Room to the secluded outdoor terrace — offer an inviting backdrop for gatherings of up to 50 guests. Whether you’re planning a milestone celebration, rehearsal dinner, welcome party, or a simple evening among friends, our team brings warmth, care, and a touch of Shelter Island charm to every detail.

Surrounded by lush greenery and the relaxed elegance of our historic property, your event becomes more than a moment — it becomes a memory. Let us help you create something unforgettable.

Live Music

9 - 11pm

Celebrate the spirit of Shelter Island with live music every Saturday at The Chequit, featuring talented local musicians from across the East End. From laid-back acoustic sets to vibrant performances, each week brings a new sound to our charming historic setting.

Grab a cocktail, settle in, and let the music carry you into a perfect Saturday evening where community, creativity, and connection take center stage.

Calendar of events

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.