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Shelter Island Heights

The Chequit Inn

Travelzoo Staff

Why We Love This Hotel

  • "Designed for dreamy summer jaunts to the East End" (Travel + Leisure) 
  • This boutique hotel sits in an 1870s-era hostelry; Frank Sinatra and Marilyn Monroe stayed here in the '40s and '50s
  • Enjoy a complimentary breakfast on the hotel's sweeping front porch overlooking the harbor

Enjoyed This
"Nice hotel nothing there Better stay in Greenport"
26. Jun 2019 - Toms River, NJ, USA
See All 8 Member Ratings

Rooms & Rates

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This charming boutique hotel offers a tranquil but stylish destination on an island that's "just minutes from the North and South Forks, yet ... it feels worlds away" (Conde Nast Traveler). Restored in 2015, the hotel feels like a B&B, with little extra touches like free use of beach umbrellas and towels as well as illustrated maps of the island. 

Stays here are focused on couples, with a variety of King rooms available. Freshly renovated furnishings feature restored hardwood floors, luxury bedding and rainfall showers and marble-accented bathrooms. Thanks to the Chequit's hilltop location, even though the property isn't on the shore, you can still get a view of the water from the guest-exclusive wraparound porch off the lobby. And like a B&B, complimentary breakfast is served daily in the lobby, but guests can opt to have coffee and pastries delivered to their rooms free of charge. 

Located at the eastern end of Long Island, Shelter Island is "the unassuming, quietly sophisticated alternative to the flash of the Hamptons" (Forbes). A full one-third of the island is a nature preserve, meaning there's plenty of bicycling, hiking and water activities like kayaking or paddleboarding -- or just hang out on one of the island's beaches or watch sailboats and yachts cruise in and out of the marinas. 



  • Bar
  • Newspaper / magazines
  • Restaurant
  • No pets allowed
  • Extra beds (fees apply)
  • 100% smoke-free
  • No elevator / lift


  • Concierge service
  • Room service (limited hours)

Room amenities

  • Air-conditioning
  • Central heating
  • Fridge


  • Complimentary Internet access
  • Complimentary Wi-Fi throughout the hotel


  • Hair-dryer
  • Separate shower
  • Luxury toiletries


  • Complimentary parking
  • Off-street parking


Check-in: Minimum age required to check in: 21.

The front desk is open from 8am to 7pm daily. Please call to arrange a check-in time, including for arrivals after 6pm.

Checkout: Standard Time is 11am.

Children and additional guests: Children 16 or under stay free of charge when using existing bedding.
Cot available upon request: free of charge.

Extra bedding (air mattress) available upon request: $50 USD plus tax, per night.
Cribs/ Pack 'n Play and air mattresses are based on availability.
Rates are based on double occupancy. Maximum occupancy for all rooms is 2 guests.

Additional details: All rates include a breakfast prepared fresh each morning, complimentary WiFi and on-site parking.

The restaurant (Red Maple) is closed seasonally from the beginning of November until the middle of May. 
The restaurant will reopen on May 18, 2019.

Roll in shower is available on request/per availability.

Have a Question? Contact Travelzoo.

Customer Service available Mon-Fri, 10am-6pm AET

Rates may vary by date, are subject to availability and are not guaranteed until your purchase is complete.

Please note: Some amenities and services may not be available in all rooms or may incur an additional charge. All prices stated have been verified at the time of publication and may vary at the discretion of the hotel.

Enjoyed This
(8 Member Ratings)
Ratings & reviews reflect verified member feedback for The Chequit over the past 15 months.
4.4 Ambiance
5.0 Location
4.4 Rooms
5.0 Quality of Service
4.6 Value for the Money
Show Reviews
Enjoyed Most
Nice hotel nothing there Better stay in Greenport
Gale 26. Jun 2019 Toms River, NJ, USA
Enjoyed Most
Susan 18. May 2019 Greenlawn, NY, USA
Enjoyed Most
Ambiance. Staff
Michael 09. May 2019 PORT JEFFerson, NY, USA
Enjoyed Most
Lovely hotel in a very convenient section of Shelter island. Staff was super friendly and responsive. We had a great experience!
Stephen 07. May 2019 New York, NY, USA
Enjoyed Most
Well-appointed facility. Very helpful staff.
Other Comments
I will stay here again!
Jennifer 28. Apr 2019 BAITING HOLLOW, NY, USA

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