The Chequit

Relaxed, summer-chic, cozy

23 Grand Ave. Shelter Island Heights


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At a Glance

Shelter Island’s charming The Chequit is a Long Island escape that feels delightfully more low-key than the Hamptons (but those wishing to take day trips to the South Fork can do so easily; Sag Harbor is about 20 minutes away by car).

Indagare Loves

  • Enjoying meals on the beautiful terrace, which features string lights hanging from the trees
  • The relaxed atmosphere on Shelter Island
  • The Terrace suite, which has a spacious private patio


Just a 10-minute ferry ride from both Long Island’s North Fork and Sag Harbor, Shelter Island’s charming The Chequit is housed in a white-washed building that dates to 1872. While the bucolic hotel, open year-round, is not located on the beach, it has all the other elements for a quiet summer escape: décor featuring pinks and grays, delicate furnishings and a restaurant that serves seasonal fare and has a terrace with string lights hung from the trees.

The Chequit’s 37 rooms feature a country-chic aesthetic with restored wood floors, soft yellow furniture, pink-and-grey walls, minimalist gold furnishings and white-tiled bathrooms with rainfall showers and C.O. Bigelow products. One of the most charming abodes is the Terrace suite, which boasts a large private roof deck with string lights, a swing chair and dining table.

A cozy countryside inn, the Chequit offers just a handful of amenities including a daily breakfast that can be enjoyed in your room (at no additional cost), in the main building or on the beautiful white terrace, which offers views of Shelter Island Heights. The Chequit’s main restaurant, Red Maple, is open for brunch, lunch and dinner during the summertime and serves seasonal dishes like grilled fish tacos, shrimp and grits and herb roasted chicken with butternut squash and swiss chard. Guests headed to the beach for the day can stock up on to-go goods like chickpea salad, pastries and coffees at White Hill Café.

Who Should Stay

Travelers looking to experience an old-world summer escape from the comfort of an idyllic countryside inn.

Written by Emma Pierce

What's Nearby

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