The Chequit blends coastal charm with timeless sophistication. This historic boutique hotel, originally built in 1872, offers an inviting mix of vintage elegance and modern comfort. Guests can unwind in thoughtfully designed rooms, savor locally inspired cuisine, and enjoy the relaxed pace of island life. With its prime location just steps from the ferry and local shops, The Chequit provides a serene yet connected getaway in the Hamptons. Historic architecture lovingly restored with modern touches On-site boutique offering curated local goods and gifts Private event spaces ideal for intimate weddings and celebrations Proximity to nearby beaches and nature preserves
The Chequit offers Events allowed, Restaurant, Free WiFi, Bathrobes, Eco-friendly toiletries, Towels provided, Premium bedding, Air conditioning, Blackout drapes/curtains, In-room safe, Slippers, Mini-fridge, Cable TV service, Flat-panel TV, Bicycle rentals, Library, Outdoor furniture, Bar/lounge, Electric car charging station, Parking onsite, Wheelchair-accessible parking available, Accessible property, Fireplace, Garden, Terrace, Daily housekeeping, Wifi Available, Wheelchair accessible.
The Chequit is located at 23 Grand Ave, Shelter Island Heights.
The Chequit has an average rating of 4.1 out of 5 based on 193 guest reviews.
1 King Bed
Summer House Large
1 King Bed
Summer House Standard
1 King Bed
Main House Loft Suite
1 King Bed
Main House Master Suite
1 Queen Bed
Summer Cottage Suite
1 King Bed
Main House Washington Suite
1 King Bed
Main House Large
1 King Bed
Main House House Standard
1 Queen Bed
Summer Cottage Standard
1 King Bed
Summer House Suite




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The Chequit blends coastal charm with timeless sophistication. This historic boutique hotel, originally built in 1872, offers an inviting mix of vintage elegance and modern comfort. Guests can unwind in thoughtfully designed rooms, savor locally inspired cuisine, and enjoy the relaxed pace of island life. With its prime location just steps from the ferry and local shops, The Chequit provides a serene yet connected getaway in the Hamptons.
The Chequit is undergoing a significant revitalization, with recent renovations focusing on the hotel and restaurant. Recent reviews highlight improvements in service, food quality, and overall ambiance, suggesting a renewed focus on luxury and guest experience. However, some guests have experienced issues with service speed and room maintenance.
Great to see the renovation and revamped service / menu. The island needs this place to work and it finally seems to be. Thanks to Yadihel, Daria and Edgardo for fun evening. Looking fwd to next visit.
Yady at the bar and Daria, the host at the restaurant, were amazing. Daria made sure we could order food when we arrived close to closing time and Yady was a lovely, helpful and gracious server. The food was delicious and we are so excited to support the new team. Fingers crossed.
We just stayed here for the very rainy Memorial Day weekend and were blown away. The hotel and restaurant have just opened with new owners, and the food was unbelievable. I enjoyed probably the best sea bass I've ever eaten and my wife adored her linguine with little neck clams. Since they've just opened, there are only a few delicious entrees to choose from - more in the weeks to come. But the starters absolutely blew us away. The meatball app was killer (I'm still dreaming about the sauce) and the humbly named "tomatoes on toast" is the Chequit's unique take on bruschetta that should NOT be missed. The cocktails were a delight and the wine list is expansive. Even though the rain spoiled it for us, there are gorgeous outdoor spaces all over the property with swinging chairs for coffee and a morning read or fire pits for evening cocktails, and bikes are available to explore the Island. Next door, the old drug store offers a really tasty diner-counter breakfast and a shop where sun-baked tourists can find anything they could possibly need on holiday. This place is an absolute gem. Book it now before the summer crowds get wind of it!
The restaurant delivers an exceptional fine dining experience that matches the luxury of the hotel itself. From the elegant setting to the attentive service (thank you Liz!) and carefully executed dishes, everything feels thoughtful, refined, and memorable. The menu shows real culinary skill, with well-balanced flavors, high quality ingredients, and presentation that feels worthy of a special occasion. What stands out most is how seamlessly the restaurant fits into the hotel experience, making it ideal for guests who want top tier dining without leaving the property. Thank you Chequit staff!
The best value on Shelter Island for 5 star accommodation. Great food,incredible flavor. Locals are wonderful at the bar. The artwork is beautiful. The café is a nice place to relax. Sit outside and enjoy the beautiful harbor front across a wonderful park.
Why oh why does it take 45 minutes to get a drink EVERY TIME? When there are only four patrons and two bartenders. Oh, never mind, it's closed again.
Dining can be inconsistent, but they get it right mostly. Recent steak dinner was excellent. Convenient place for Americana cuisine.
A remarkable hotel and restaurant. Multiple restaurants on property. A luxury hotel. We didn't stay there, we had coffee at the cafe. Delicious, lavender, homemade iced coffee. Delicious. The grounds are gorgeous. Go see them. Tell em Barsnobs sent ya!
We had the best time- perfect hotel for a weekend getaway. The staff is incredibly kind and attentive. Shoutout Chris at the front desk.
We paid over 700 dollars for one night on a Saturday. Our tv was broken and would not work. We were told maintenance would come and fix it, but no one ever came. It was a rainy weekend so that was very unfortunate. Our AC also did not work so our room was stuck on 75. We called the front desk about this issue as well and nothing was done about it. Very upsetting for spending so much money and having the basic amenities being broken. All we got was a “sorry” upon checking out. Definitely recommend staying elsewhere.
This property is not bookable on our official site, you will be taken to the listing externally.