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23 Grand Ave, Shelter Island Heights, Shelter Island, NY 11965-2000
Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
Traveler (62)
Dining (6)
Room & Suite (5)


#2 of 4 B&Bs / Inns in Shelter Island Heights
Following an extensive renovation this historic 36-room inn will redefine the concept of the traditional bed and breakfast with a fresh no rules approach. Guests can expect a new restaurant, grab and go cafe and local retail outlet. All rooms have been fully renovated with crisp, fresh amenities and new private bathrooms. Exclusive use of private terraces for all guests.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Free breakfast
Baggage storage
Non-smoking hotel
Private check-in / check-out
Laundry service
Bar / lounge
Breakfast in the room
Wine / champagne
Outdoor furniture
Sun terrace
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Room features
Air conditioning
Bottled water
Room types
Bridal suite
Non-smoking rooms
Family rooms
Good to know
Historic Hotel
Languages Spoken


Full view
39Car recommended
Grade: 39 out of 100
11Restaurantswithin 0.75 miles
0Attractionswithin 0.75 miles
178Reviews6Q+A30Room tips
Traveler rating
  • 129
  • 27
  • 16
  • 4
  • 2
Time of year
Traveler type
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rdubsnyc wrote a review Oct 2019
Bloomfield, New Jersey5 contributions2 helpful votes
The website shows very vibrant pictures of the property and the charm and our love of Shelter Island is what led us to book our stay. Unfortunately, we were only able to stay one of the two nights due to an unavoidable conflict. The general manager, Jason, was nice and helpful upon our arrival and brought my wife some tea as she had a cold (which was very thoughtful). The standard king room was a bit on the smaller side. It did have a fridge, which was in the closet though as well as a stand-up shower in the bathroom. What shocked me a bit was that aside from beach hat a scarf there was no other character to the room (nothing on the walls) - one of our favorite aspects about B&B's or Boutique hotels is the character and charm. Breakfast was delicious, but the layout for seating was a bit more segregated than what i am used to at similar places. In order to eat comfortably we had to eat outside and were saddened that we could not engage in discussion with the other guests - perhaps this changes based on time of year and how booked they are at the time. We also noticed that the porch furniture and mats were a bit worn down - perhaps since it was towards end of season it will get some love in the new year, it looks quite nice in the website photos. Overall, the sterile feel of the room really felt more like a hotel with a breakfast rather than a Boutique B&B.
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Date of stay: October 2019
melhuk2us wrote a review Oct 2019
Nesconset, New York2 contributions
My room was perfect, the bed was so comfortable, and the people were incredibly kind. The breakfast tasted great and was plated beautifully. It is a very pretty and quaint island, we went in October. It was a fantastic experience
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Date of stay: October 2019
Response from Jason M, General Manager at The Chequit
Responded Oct 19, 2019
Hi Melanie! We are thrilled to hear you enjoyed your stay at The Chequit! October is one of our favorite months on SI! Looking forward to welcoming you back for another perfect stay. Very Best, Jason
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halfmoonguides wrote a review Sep 2019
Brooklyn, New York38 contributions13 helpful votes
We stayed here over our wedding weekend and were blown away by the beautifully renovated rooms and friendly service. The breakfast was also delicious - eggs, coffee, freshly baked muffins and chia pudding! (The restaurant had closed for the season - but breakfast is provided.) If you're staying on Shelter Island and want a special treat, definitely check it out.
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Date of stay: September 2019
MoveBubble wrote a review Sep 2019
Brisbane Region, Australia2 contributions
I stayed at The Chequit over the Labor Day weekend. I didn't have a car and had not visited Shelter Island before. The place was just perfect with chairs on the verandah to read, have a wine in the afternoon or to just wander up the street for a coffee or bite to eat. The rooms are nicely decorated and whilst the air conditioning can be loud, you wouldn't expect any different in a historic hotel so I saw it as part of the charm. I cannot thank Jason enough for his warm welcome, recommendations and friendliness every day. He made the stay very pleasant even though I'm sure he was run off his feet at times. I will definitely visit again and will be recommending this to anyone visiting.
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Date of stay: September 2019Trip type: Traveled solo
finlaynyc wrote a review Aug 2019
Babylon, New York2 contributions
Great family weekend. Love the character and the Red Maple restaurant was off the charts. Chef Paul 10+ rating from me my wife and my daughter. We’ve eaten at a lot of restaurants and this could’ve been the best meal we’ve had. I recommend this restaurant highly
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Date of stay: August 2019Trip type: Traveled with family
Response from Jason M, General Manager at The Chequit
Responded Oct 19, 2019
Thank you for the amazing feedback! We are thrilled to hear you enjoyed Red Maple. Looking forward to welcoming you back for another delicious meal!
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$218 - $530 (Based on Average Rates for a Standard Room)
chequit hotel shelter island
United StatesNew YorkLong IslandHamptonsShelter IslandShelter Island Heights
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Frequently Asked Questions about The Chequit
What are some of the property amenities at The Chequit?
Some of the more popular amenities offered include free wifi, free breakfast, and an on-site restaurant.
What food & drink options are available at The Chequit?
Guests can enjoy free breakfast, an on-site restaurant, and a lounge during their stay.
Is parking available at The Chequit?
Yes, free parking is available to guests.
What are some restaurants close to The Chequit?
Conveniently located restaurants include Marie Eiffel Market, Stars Cafe, and The Flying Goat Restaurant.
Are there any historical sites close to The Chequit?
Many travelers enjoy visiting Oysterponds Historical Society (4.6 miles), Shelter Island Historical Society (1.9 miles), and The Village Blacksmith (1.3 miles).
Does The Chequit have any great views?
Yes, guests often enjoy the harbor view available here.