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
Parking on site
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Historic Shelter Island inn turned chic boutique beach break, featuring minimalist-luxe rooms, a restaurant, and a café
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.
The Chequit Inn
23 Grand Ave
Shelter Island Heights, New York 11965
How to Get There
Flights are available to John F. Kennedy International Airport (JFK) and East Hampton Airport (HTO) via connecting flights from major U.S. cities on a variety of carriers. The property does not offer private car transfers to/from JFK, about 80 miles away, or HTO, about 12 miles away. Taxis to/from JFK are approximately $300, each way, and to/from HTO approximately $40, each way. For guests who rent a car, self-parking is available on-site at no additional cost. A private 45-minute charter flight via StndAIR is available from the 23rd Street New York Skyports Marina to HTO or Crescent Beach on Shelter Island for approximately $550 per person, each way. The North Ferry transfer from Long Island to Shelter Island is approximately $10 per car, plus $1 for each additional passenger, each way; the first North Ferry boat departs Greenport Village at 6 a.m., and the ferry runs every 10 to 20 minutes until 10:30 p.m. (Then it runs every 30 minutes until at midnight, or 12:45 a.m. on the weekends.)