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What We Love

  • The reimagining comes courtesy of clever hoteliers, Kevin O'Shea and David Bowd
  • Guests can stay in the 31 guestrooms in the Main House and Cottage or in the six-bedroom Summer House
  • The clean-lined, minimalist style is the opposite of country chintz
  • There's already buzz about the upcoming restaurant and boutique
  • Read more on this summer's hot new hotel

What To Know

  • Free WiFi
  • Children 16 and under are not permitted
  • The inn is also home to a café, retail boutique, and restaurant, Red Maple
  • The classic whitewashed inn dates back to 1872
  • There's a hotel parking lot; one spot is reserved for each room


  •  Free WiFi
  •  Parking On Site
  •  Restaurant
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Beach Hotels New York Romance South Fork The Hamptons Trip Ideas Weekend Getaways property Bedroom home living room cottage


Historic Shelter Island inn turned chic boutique beach break, featuring minimalist-luxe rooms, a restaurant, and a café

The Lowdown

Imagine the beachy Hamptons cottage of your dreams — it probably looks something like this brand new Shelter Island gem. Think lashings of whitewashed vintage charm, pared-back decor featuring restored hardwood floors, heavenly white feather duvet beds and perks like sea views and clawfoot tubs in some rooms. The reimagining comes courtesy of hip hoteliers Kevin O’Shea and David Bowd, the design-savvy duo who have been reinventing the B&B (see their already award-winning Salt House Inn in Provincetown, Massachusetts). The Chequit is headed for the same white-hot status. The classic whitewashed inn, which dates back to 1872 and is located in Shelter Island Heights on the island’s north side, consists of a Main House, Cottage and a shabby-chic Summer House containing six bedrooms. Breakfast, which can be taken in the historic lobby, on the front porch or in bed, features local and seasonal ingredients, and everything is made fresh and in-house.

In the Area

Mingle with Shelter Island locals at the Saturday farmers market, which is held during the summer season at the 1743 James Havens Homestead on South Ferry Road. Some of the produce will likely be from Sylvester Manor, an educational farm set on a bucolic 1652 homestead with a beautiful house, windmill and grounds that visitors can explore; the manor also holds regular events, including farm-to-table dinners. Cheat on the Chequit briefly by stopping in for a rosé and a plate of ceviche at Andre Balazs’s barefoot-chic hotel, Sunset Beach, where you’re sure to rub shoulders with the island’s vacationing beau monde. Finally, forage for treasures at one of the town’s antiques stores; Marika’s stocks top-quality vintage finds, from Danish Modern chairs to stone cherubs for the garden.

How to Get There

The Chequit Inn
23 Grand Ave
Shelter Island Heights, NY 11965 United States


A new favourite

I stayed at The Chequit over the Labor Day weekend. I didn't have a car and had not visited Shelter Island before.

The place was just perfect with chairs on the verandah to read, have a wine in the afternoon or to just wander up the street for a coffee or bite to eat.

The rooms are nicely decorated and whilst the air conditioning can be loud, you wouldn't expect any different in a historic hotel so I saw it as part of the charm.

I cannot thank Jason enough for his warm welcome, recommendations and friendliness every day. He made the stay very pleasant even though I'm sure he was run off his feet at times.

I will definitely visit again and
will be recommending this to anyone visiting.


Great family weekend. Love the character and the Red Maple restaurant was off the charts. Chef Paul 10+ rating from me my wife and my daughter. We’ve eaten at a lot of restaurants and this could’ve been the best meal we’ve had. I recommend this restaurant highly

We'll keenly be back !

My sister and I have been more then delighted to find this little hidden gem on Shelter Island after days of roaming with over-pricey (and unattractive) lodging within a certain vicinity to Montauk. The breakfast offer at the Chequits is a major perk. Rooms are tidy and fresh, the amenities have been greatly selected. Some refillable containers in the shower unit would be a great step towards a more sustainable offer. The innkeeper proposes some chairs and umbrellas for beachtiming. We are keenly considering coming back !