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The Chequit

  • Hotels
  • Long Island
  • 4 out of 5 stars
  • Recommended
  1. The Chequit
    Photograph: Courtesy Zack DeZon
  2. The Chequit
    Photograph: Courtesy Zack DeZon
  3. The Chequit
    Photograph: Courtesy Zack DeZon
  4. The Chequit
    Photograph: Courtesy Zack DeZon

Time Out says

4 out of 5 stars

If you’re a historic inn that’s over 150 years old and you don’t look a day over 150 weeks, you’ve got to be doing something right. That’s certainly the case with The Chequit, a gracious throwback property located on bucolic Shelter Island. A recent renovation of the building, along with its 19 guest rooms, has brought the resort into the 21st century while retaining enough of its original charm to feel firmly grounded in the past. It’s an excellent homebase for both couples and families looking to explore the laid-back charm of the island.

Surrounded by hydrangeas in bloom and fronted by a gorgeous, massive patio, the renovated building welcomes guests with a soft, off-white color palette and welcoming custom-made furniture. Adirondack chairs and woven hanging seating areas can be found on the porch and many of the guestrooms now contain some truly envy-inducing tubs. Overall, there’s an elevated and relaxed coastal vibe. Some of the tables on the patio even boast views of the nearby harbor. 

There are two distinct dining rooms on the property and one café: Weakfish, The Tavern and Height Café & Wine Bar. Weakfish and The Tavern share an eclectic menu with some surprising Asian influences—Weakfish even features a sushi bar that sits eight. You may want to skip the first course and dive right into the hearty mains on the menu, but that would be a mistake. One of the best offerings is the delicious wedge salad. Meanwhile, the Heights Café serves up coffee drinks in the morning before you head out for your island adventure.

Speaking of adventure, the staff at The Chequit is more than happy to assist in providing maps, tips and itineraries for you to make the most of your stay. The service strikes the perfect balance between relaxed and helpful. However, take heed: Shelter Island may look tiny on a map, but it's probably a lot bigger than you think. Luckily, complimentary (and very cute) electric bikes are available for guests to use, allowing you to zip to all of the stunning beaches and bountiful farm stands that your heart desires. (The pedal assist also may help you look as deceptively youthful as the hotel.)


The Chequit is located in Shelter Island Heights not far from the North Ferry that runs regularly between the island and the North Fork town of Greenport. It’s surrounded by one-of-a-kind, strikingly preserved Victorian vacation homes and right next to a small downtown with a few stores and cafés.


Unlike many other hotels on Shelter Island, The Chequit is not located on a beach. However, there are plenty nearby worth checking out. Sunset Beach is a bustling hotspot with harbor views and lively nightlife. Those looking for a dinner out should head to Léon 1909, one of the island’s best new restaurants. Don’t leave without stopping by Sylvester Manor Educational Farm for some fresh produce. 

Time Out tip: 

Be forewarned: the ferry to the island only takes cash and checks!

Will Gleason
Written by
Will Gleason


23 Grand Ave.
Shelter Island Heights
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