Members Recommend
Very Good 124 Reviews
Jetsetter Approved
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.
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 124 Reviews
US Golf Open
Reviewed 1 day ago

Our first visit to this part of the country and our first experience with riding the train, etc. I received two phone calls and two emails prior to trip asking if I needed any assistance in making my visit as smooth as possible. They walked me through the process and made me feel so special. The cottage was beautiful and clean. Super cozy for couples but family friendly for sure. Highly recommend this place!

Lovely stay!
Reviewed 6 days ago

Beautiful little B&B, very cozy and conveniently located. Terrific porch and a garden full of blooming plants. Great breakfast too, considering that this is not strictly a hotel. It's a pretty quiet place so get ready to relax. We enjoyed our stay!

Wonderful Memorial Day Honeymoon!
Reviewed 3 weeks ago

My husband and I got married this past Friday and enjoyed Saturday-Monday at the Chequit! It was the perfect weekend get-away. The hotel itself is very sweet, and the breakfast is extremely fresh and delicious. Shelter Island in general was a lovely place to bike and enjoy local restaurants, but all was made even lovelier by Jason, the manager and another young woman who's name we didn't catch. They were both so friendly and considerate and made us feel welcome from start to finish. Thank you to the Chequit for sharing in our joy this weekend! We will definitely be back one day!

Girls weekend getaway
Reviewed 3 weeks ago

A girls weekend getaway compliments of my daughter proved to be the most relaxing, restful weekend. The Chequit is quaint, CLEAN, comfortable. Jason and his team were PHENOMENAL in making you feel welcome and as the only guests staying on property. Breakfast was delicious and plentiful. Coffee and dessert at the Red Maple delicious! Cannot say enough about the quality of service! Cannot wait to return!

Ahhh, the Charming Chequit
Reviewed 1 month ago

True, it was off-season (mid-May), but we've stayed there several times during high season, and the Chequit gives us every reason to return again and again.

The Chequit itself is such a fabulous place — the breakfasts were fresh, inventive, and oh-so-scrumptious (and we’re foodies). Our room was so comfy cozy — the bed linens, so cushiony soft and oh, the indulgence of those pillows! Housekeeping was on its toes for sure — everything was immaculate and the bathroom was like a well appointed spa.

General Manager Jason Mancuso could not have made it more wonderful for us! He was simply superlative. Jason had emailed us beforehand, asking about allergies (which I appreciated as I have a fatal food allergy), and welcoming our requests about things to do, etc. How thoughtful! And the difference between Jason’s email and the standard inquiries automatically emailed by other places is that Jason meant every word and delivered on arrival. He was warm and welcoming, sincere but not sappy, most cordial, and had a real zest for the area which he knew very well. Every suggestion of his was a winner. His gracious hospitality made our visit over the top!