Members Recommend
Very Good 145 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 145 Reviews
Great all year round!!
Reviewed 1 month ago

My boyfriend and I have stayed here twice, once in the height of summer, once in the depth of winter. For both stays the hotel staff (especially Allie and Jason) were fantastic and always went out of their way to make our stay. The building is old and a bit creaky but that is what makes it so charming (they provide earplugs but even as a light sleeper I never needed them). The breakfasts are excellent. The lobby and porch are so comfortable they are hard to leave. It is a great location on Shelter even if you do not have a car. There are plenty of places to walk for food and its very close to the north ferry. If you can, book a suite as they have awesome claw foot tubs. We look forward to returning again soon!

A cozy & serene getaway
Reviewed 2 months ago

My husband and I were delighted with our latest stay at the Chequit Inn. I felt compelled to write this review because of the friendly, generous and courteous service provided to us by the manager, Jason. We were thrilled to be staying on the beautiful top floor terrace suite, outfitted with chilled water and wine for our birthdays. The main floor common area is thoughtfully decorated with holiday details, the fire place is roaring, and music of the Nat King Cole variety was piped in. It’s the perfect place to sip a nighttime drink after dinner at Isola, two doors down. My bed was so comfortable as to be heavenly, and breakfast (asparagus, tomato, goat cheese omelet, pumpkin puff pastry, yogurt with fruit and granola, fresh coffee) was a tasty start to the day. In addition, it was just so nice to converse at length with the manager and the chef, and to have that indelible experience that can only be associated with a great B & B. We’ll be back!

George Washington may have slept here....
Reviewed 3 months ago

I think I’m glad I didn’t leave the reviews of this place before we stayed here. All the negatives were true. There are big gaps under the doors, the plank flooring provides no insulation anywhere in the hotel (so you hear everyone on the stairs going up and down AND walking above you), the wind whistles through the windows and yes, you can hear what other people are saying in rooms above and to the sides of you. The rooms are very small (12x18?), it was expensive $300/nite) and there are no TVs here. The bathrooms have been updated nicely. This is NOT a place for privacy (romantic evenings are out of the question). That said, it IS a very cute old hotel that has a lot of charm. Breakfast was ok- cinnamon bread and English muffins, chia pudding (?), watermelon (a cheap fruit option in my opinion when blueberries are so plentiful now), quiche, banana muffins, oj. I guess we just aren’t B&B people....

Fall Getaway
Reviewed 4 months ago

My Girlfriend and I arrived to Shelter Island in the middle of a Nor'easter! Since there are no Ubers or reliable cabs we were stranded. Luckily Jason, the proprietor, was kind enough to come pick us up. From the start to finish Jason and Aly were very helpful and hospitable. We had a fantastic dinner right next door at Isola and finished off the night with a glass of wine in The Chequit's warm living room. I would highly recommend staying here for a relaxing getaway.

Review from our stay in September 2018
Reviewed 4 months ago

We were contacted by The Chequit team before our stay to get information about us - our expectations had risen from this tiny detail. Unfortunately what followed was a disaster. Despite specifically requesting a room in the cottage 2 weeks ahead, we were given the most noisy room in the main building and the on site team (Aly?) seemed quite unfriendly and not willing to change the room even though rooms were available in the cottage. Eventually after a lot of discussion our room was changed to the quiet cottage which had been our original request. It seemed like they were trying to keep all guests in the main building rather than the cottage since it was low season, maybe saving on cleaning costs?? Aly pretended to give us an upgrade when in reality it was a massive downgrade.
The inn does not look like anything in the pictures- the furniture in the veranda is soiled and full of stains and food crumbs and there was hair in the bedding in the room. The breakfast was hardly what you expect for the price. Overall even though we loved Shelter island and would return to the island, our stay at Chequit was quite disappointing. We found the place overpriced and not able to deliver what it promises on the website.
Usually I do not write reviews, in this instance I think management needs to know what is happening on site and how their staff behave with guests. If you are going to charge New York prices, you have to deliver a service worth the value.