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Very Good 1892 Reviews
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This Hotel meets our standards
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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
Disclaimer: This content was accurate at the time the hotel was reviewed. Please check our partner sites when booking to verify that details are still correct.
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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


Could Use a Bit of Love

The website shows very vibrant pictures of the property and the charm and our love of Shelter Island is what led us to book our stay. Unfortunately, we were only able to stay one of the two nights due to an unavoidable conflict. The general manager, Jason, was nice and helpful upon our arrival and brought my wife some tea as she had a cold (which was very thoughtful).

The standard king room was a bit on the smaller side. It did have a fridge, which was in the closet though as well as a stand-up shower in the bathroom. What shocked me a bit was that aside from beach hat a scarf there was no other character to the room (nothing on the walls) - one of our favorite aspects about B&B's or Boutique hotels is the character and charm.

Breakfast was delicious, but the layout for seating was a bit more segregated than what i am used to at similar places. In order to eat comfortably we had to eat outside and were saddened that we could not engage in discussion with the other guests - perhaps this changes based on time of year and how booked they are at the time. We also noticed that the porch furniture and mats were a bit worn down - perhaps since it was towards end of season it will get some love in the new year, it looks quite nice in the website photos.

Overall, the sterile feel of the room really felt more like a hotel with a breakfast rather than a Boutique B&B.

Wonderful place and wonderful people
Melanie H

My room was perfect, the bed was so comfortable, and the people were incredibly kind. The breakfast tasted great and was plated beautifully. It is a very pretty and quaint island, we went in October. It was a fantastic experience

Wonderful Shelter Island retreat

We stayed here over our wedding weekend and were blown away by the beautifully renovated rooms and friendly service. The breakfast was also delicious - eggs, coffee, freshly baked muffins and chia pudding! (The restaurant had closed for the season - but breakfast is provided.) If you're staying on Shelter Island and want a special treat, definitely check it out.