97%
Members Recommend
4.5
Very Good 167 Reviews
Jetsetter Approved
This Hotel meets our standards
This hotel meets our standards, but we haven't stayed yet

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

Amenities

  •  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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Overview

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

Reviews

Diamond in the rough
CaptPhilly

Can't say enough about Jason at the front desk! When we arrived, he greeted us with his awesome personality, he couldn't do enough for us! The bartender on Wednesday night was also awesome! (silly us failed to get her name, sorry) Definitely will stay there again when we ever get back to Shelter Island.

Anniversary celebration
jsue

Our children gave us a mini vacation to celebrate our 40th anniversary and chose The Chequit! We loved the serenity of your hotel. Our room was upgraded -very clean and quaint!. A bonus was no tv in the room! The staff were so helpful and friendly- giving us tips on beaches and restaurants and having breakfast included allowed us to have a stress free time. Enjoyed the wine during "happy hour". A great big thanks for to The Chequit.

The staff is amazing and so friendly.
Stylegirl3

When you walk in.. the stress melts away. The Chequit is in a perfect location and is so cute and clean. Breakfast was one of my favorite parts.. I recommend staying here to just detox and recharge from life!