Members Recommend
Very Good 154 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


  •  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.
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


4.5 Very Good 154 Reviews
Made our engagement weekend perfect
Reviewed 2 weeks ago

Jason and the entire team at The Chequit made our engagement weekend perfect! Our Terrace room was beautiful and and made for the ideal location for the proposal. The staff was informative, accommodating, and such a pleasure. We'll definitely be back.

Great Early Spring Stay
Reviewed 3 weeks ago

Spent a beautiful early spring day at The Chequit. Hosts were very friendly and accommodating. Wine on the porch, overlooking the beautiful harbor, on a gorgeous day can't be beat. We'll be back in the fall.

A special place...
Reviewed 4 weeks ago

Warm, cozy, beautifully decorated Inn with a family-like and convivial vibe. It is conveniently located a few minutes away from the North ferry and our room had a beautiful view of the water. The service and hospitality are outstanding! We found a handwritten note and they generously offered us a glass of wine for my husband's birthday. Not to mention the most lovely & healthy breakfast buffet surrounded by other guests, soft jazz music and a fireplace. It was an absolutely perfect escape from New York!

Little gem, simple, lots of character
Reviewed 1 month ago

Stayed here one night with my husband. Simple, clean room. No TV- love that! Couple of local shops and restaurants I walking distance. On site breakfast was outstanding. Just a heads up...at first we sat at a table on lovely porch but headed inside because of bees! Overall though, you will be happy here. Next summer we will stay for 2 nights!

Perfect Vacation~
Reviewed 1 month ago

The Chequit is our most favorite place to vacation! We go every year to celebrate our anniversary b/c there's no better place to recharge, refresh and receive all you want out of a vacation!! Jason and his staff are friendly and helpful. The rooms are clean and so comfortable that we even tried to purchase the bed. The ambience in the morning sets the perfect mood for your day and the food is absolutely delicious! We can't wait to return~