The Chequit

Hotel · Shelter Island Heights

The Chequit

Hotel · Shelter Island Heights

2

23 Grand Ave, Shelter Island Heights, NY 11965

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Highlights

Asian & tavern dishes, sushi, filet mignon, lobster rolls  

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23 Grand Ave, Shelter Island Heights, NY 11965 Get directions

thechequithotel.com
@thechequit

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23 Grand Ave, Shelter Island Heights, NY 11965 Get directions

+1 631 749 0018
thechequithotel.com
@thechequit

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Aug 7, 2025

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@eater

16 Late Summer Dining Spots in the Hamptons

"Built in 1872 as a meeting hall, the dining room at this iconic hotel that played host to Marilyn Monroe and Arthur Miller, has an expansive outdoor seating area and large wooden center bar with an antique billiard table. Asian and tavern dishes share a menu that ranges from an extensive sushi selection to filet mignon and lobster rolls." - Beth Landman

https://ny.eater.com/maps/best-restaurants-hamptons-guide
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@cntraveler

What's New on Shelter Island and Long Island's North Fork This Summer

"While Shelter Island was originally a favorite summer retreat for old-money families and notables like Marilyn Monroe, Arthur Miller, and the Kennedys, hoteliers are now turning the tucked-away island into a year-round destination. The Chequit, owned by the same family that recently reopened Peconic Bay Vineyards, reopened last summer after a two-year renovation—just in time to celebrate its 150th anniversary. The hotel’s makeover includes a luxe update to its existing 19 guest rooms, an addition of 16 more, plus a revamp of their famed restaurant The Tavern, now overseen by chef Darren Boyle, formerly at Salt, another notable restaurant on the island. Two new food concepts were also introduced: Weakfish, specializing in New Asian cuisine and Asian-inspired cocktails; and Heights Café, which offers coffee and pastries until mid-afternoon."

https://www.cntraveler.com/story/things-to-do-north-fork-shelter-island
View Postcard for The Chequit

Companion687603

Google
Hotel is undeniably beautiful - stylish decor, spotless rooms, great location. Unfortunately, this is where the positives end. The walls are paper thin so you can hear every hallway conversation and every door opening and closing at all hours of the night. If you’re a light sleeper or hoping for a peaceful retreat, this may not be the right fit.

Haley Conn

Google
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.

Maia Brownson

Google
We had the best time- perfect hotel for a weekend getaway. The staff is incredibly kind and attentive. Shoutout Chris at the front desk.

Stay43051653560

Google
Amazing, amazing 6 oyster platter, watermelon salad and Scottish salmon! Views were great, staff was quick and friendly.

Karin Krueger

Google
The fried calamari was done perfectly. Tender, not overcooked like in so many restaurants. And a heaping bowl full.

sharon butler

Google
We came here for lunch as part of a group trip on a bus. The food was amazing but I feel the service aspect was not ready for the group. Take it we had close to 50 people but they knew we were coming. Service was extremely slow and staff seemed confused. It was off season and we were the main guests. I feel they probably were overwhelmed.

Vincent Gatto

Google
A quaint spot with a lot of attitude. The tavern/bar is a nice eating venue with a great revolving menu. Their oysters and clams were very efficient for the price. The passionfruit martini was also very tasty. The duck spring had a very unique flavor and almost convinced me to order a second round!! We took the truffle fries to go, and the taste wasn’t as I expected it, probably due to them sitting in the fridge overnight. Looking forward to my next trip back!

Henry Oh

Google
Tavern dining is always great here. Everything I’ve tried has been spot on. Fun, comfortable, and nice atmosphere. Plenty of space at tables or bar and a pool table to boot. Had a great soup special and burger last time I was here. Friendly staff.
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Matt T.

Yelp
What a great spot. Wasn't sure what to expect when booking. It looked really rustic in the pictures but it was far from that. The rooms were done over very nicely. The food was really good and the bar downstairs was a lot of fun. Staff was very accommodating and nice as well
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Echo L.

Yelp
This review is for the restaurant. The one star is for the location and the view. The service is absolutely terrible. From the maitre de to our waiter who was unprofessional, patronizing and extremely rude. And the food is really awful. It's your very basic, shitty roadside diner food that's exorbitantly priced. We ordered the $50 NY Strip. It was a supermarket bought steak cooked tasteless and served with spit out spinach and prison-style mash potato. There is no excuse for this. Every dish was questionable except for the corn soup which was very good. There are so many better places on Shelter Island to eat. Save your money and your time. This restaurant is a disaster.

Alison M.

Yelp
This is one of the worst restaurants I have been to in years. I would not recommend it to my worst enemy. I have never had a Buratta salad in my life. My husband and I had drinks two appetizers and we left. The spicy crab tacos tasted like weird tunafish, and I looked around and couldn't imagine why anyone was sitting here eating. We got up and left after our appetizers and went to a different restaurant and had a great time at Isola just next door.
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Linda G.

Yelp
My meal was DELICIOUS!!!! Full of flavor! The patio seating was magical with amazing lighting. Seats were comfortable and we were able to sit for a long time. Oh, cocktails were yummy too!
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Alex A.

Yelp
Honestly I was skeptical but our meal was delicious and service was great! The lavender lemonade is so good, as were all of the desserts. Salads were great. We have a big group and they handled it really well. I had the crabcakes, very good with a little kick of spice. Everyone enjoyed their entrees.

Daniel R.

Yelp
Great lunch today!!! Last winter I was not happy with our dinner in the tavern and gave only two stars. Really glad we came back for another visit with friends visiting the island. The arugula salad was really delicious with a substantial portion and the tuna mango tartare was excellent. Our friends enjoyed the lobster roll sandwich and salad. Nice wine list and great beer selection. Our waitress was excellent and attentive and deserves a nice shout out. We will definitely be coming back - can't beat the view of Dering Harbor on the porch.
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Terri G.

Yelp
Wine pairing dinner was great! Service was very good, food was delicious, particularly the duck ravioli. Lisa, the manager was on point-nothing phased her, nothing was too difficult. Our only criticism was that the heated porch was too cold. This was our first time here, looking forward to coming back for a Friday price fix meal.

Anna R.

Yelp
Another fabulous year We have returned to our favorite place on shelter island again another wonderful stay unfortunately the weather did not cooperate with us all week but the chequit made it so comfortable for us while we were there , one thing did change new chief aboard but have to say dinner was delicious so congrats on the new chief! Our room was great has usual most of all staff is unbelievable! We always feel so welcomed and safe there the manger is always happy to see us ! We have built such a great relationship, I've stayed at a few places at shelter island previously couldn't compare! Where very lucky to have this little piece of paradise in our lives!!!looking forward to next year!
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Sophie L.

Yelp
We had dinner here for the second time. First time all was well. Second time, this summer 2024, the service was bad! First, it was very slow and took a very long time for the waiter to take an order. Then the order was not what we asked for (medium rare steak turned well done), then before we were done 3 different servers asked to take away our food while we were clearly eating. Overall, the setting is lovely for outdoor dining but given the price and that there are other options on the island, this is not worth going back to.

Raina K.

Yelp
dont stay here if you want to relax and sleep. blasting disco music from the bar downstairs. when I complained I was told they could not ( would not ) turn it down. on top of it most of the staff spoke no english so very difficult to communicate the issue. Will not be coming back here.
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Andy H.

Yelp
Reviewing the Tavern specifically here, and after four visits (and trying to keep mind wide open) I have to say this place is a FAIL. The service staff ranges from high school and college kids on vacation, some of whom act like they are pledging a sorority while on duty, to a few able servers. If you are determined to eat here, I urge you to keep it simple and sit at a table (NOT at the bar, where the bartenders are usually highly distracted or dealing with some cognitive issues.) Speak clearly if ordering the "Chequit Burger". One time my wife & I ordered one and they brought us a "Children's Burger" which was a miserable joke for which they profusely apologized yet never followed through with a promised credit towards another meal. Not much else to say except there are other options on the island for food in this price range.
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Ruth H.

Yelp
Planned a one night anniversary trip to Shelter Island. Made the reservations and all set. I wish i had opted for the insurance. Two days before our trip, my husband came down with Covid. Requiring five days quarantine. I called to see if i could rebook later in September. Was told "Sorry no refund(wasn't asking for one) and no rescheduling". I asked if they preferred we come? No response. It was all very civil. However, illness should be taken into account.

Dan R.

Yelp
Been here a number of times and usually come away satisfied. But not tonight. Service was great, but the poke bowl was very disappointing. Although it listed a number of ingredients on the menu, all I could find was a very tiny amount of salmon and a ton of white rice. Nothing else was in the bowl, really. $24 for this bowl was not worth it.... My wife had the chirashi bowl which was actually quite delicious and loaded with fresh vegetables. I hate to give the restaurant a negative review but really I feel it is appropriate tonight. We will return since we live on the island but I will order something else.

Maureen C.

Yelp
Excellent service and relaxing setting. Brunch menu offered many options and Bellini was delicious!

Andrew E.

Yelp
Restaurant review. Great ambiance. Only about 2/3 full on a Thursday night. About 20% of the entree items were unavailable. Of the 3 type of oysters on the platter only 1 type was available. Would have liked having a couple of $30ish wines available. The wait staff was phenomenal so kudos to them. Really want to see this place work as live on island and think they will with some attentive direction.
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Bullfrog R.

Yelp
Lack luster. The napkins are black. Makes me feel dirty. We sat down and waited to order our food way too long. All the water glasses are different sizes. Spent $200 on bread, shellfish and 1 sushi roll. This location has been a problem in the past. Something in me hopes they figure it out.
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Paula V.

Yelp
Obsessed ! From the moment we walked in, renovated inside and it's such a beautiful cute boutique style hotel. You can tell it's very old from the stairs to the very thin walls and no TVs in the rooms. The service was great. The decor throughout the entire place was beautiful. Bedroom decor was super cute as well. Hotel provided beach blankets for the beach which was great and the food that was offered for breakfast was DELICIOUS! Food was great and everything all together 5 stars. Only 1. Small issue I did have is that there were a lot of bees inside the lobby area of the hotel.
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Dano O.

Yelp
As island natives, we were very excited about the reopening of the Chequit (which is gorgeous) Our first dining experience a few weeks ago was wonderful. Excellent service, delicious food and beautiful porch setting. We revisited recently with off-island friends only to be terribly dissatisfied with the service and experience (and to very be clear, not the wait-staff, which were doing their very best on a busy night) First issue (very minor) - rather long wait for drinks to arrive (but understandable on a crowded evening) Next, we ordered two appetizers - ours came quickly, albeit with no utensils But after 20 min, our friends appetizer had still had not arrived. So we just sat confused and hungry. Finally, our waiter returned quite some time later to inform us that the kitchen was now out of the appetizer that our friends had ordered!! But was apologetic and offered a replacement..... Then a remarkable reversal occurred - our friend's entre arrived (they said it was quite good), but ours never appeared - NEVER... (the tables had turned, justice was served...??). And after our friends finished their dinner, we just gave up, cancelled our main course, and left rather hungry......

Rory F.

Yelp
So we were really hoping for a good experience. Costs a couple of bucks to get over there from the mainland and me and my wife haven't been to the Restaurant for quite a while. With good friends, food ok at best , more like a pub atmosphere than a restaurant and service was just terrible. So after terrible service we asked the less then attentive male waiter, backwards cap with a lolly pop in his mouth, for the check and give him two credit cards for the split. He brings back one at $120 and one at $180, clearly not a split. "What happened". Not sure he says "just make it up in the Tip"!! "Very difficult to split a check"!. So clearly he was making sure he was going to get a undeserved $60 dollar tip after clearly sub a sub par meal and terrible service. Nice try!!!

Patti M.

Yelp
Good food, great service and atmosphere but I think the next time we go we will sit outside or further away from bar. Was very loud.

Warren R.

Yelp
Some really bad preparation. The crispy short ribs turned out to be slabs of sliced beef In a soggy coating on a bowl of rice that was neither crispy or flavorful. 3 of 5 dishes were sent back.

Liz C.

Yelp
French Fries were delicious! The rest of the food was good. The steak wasn't cooked well. Sent it back and still wasn't right. Our waitress was very pleasant!

Mary J.

Yelp
Great staff....Food awful over priced and tasteless. Surprised because how to you screw up fish & chips & halibut. Ridiculous cost of dinner for 3 for pub food $350 plus tip. But the worst thing was they seated 2 woman with 3 of the worst behaved little boys!!! One mother seemed embarrassed by the children's behavior the other basically gave us the finger. Hostess said tavern is children friendly!! Chucky Cheese has better behaved children & food. Be very interesting when kids fall on blue stone steps and need a plastic surgeon to fix their face, then the owners of Chequit can decide how child friendly they are. We are local & here year round & won't be back. Again staff was great though.

David R.

Yelp
We visited November 3rd-4th. The hotel is well located and it's public areas nice, however the room was a dirty shoebox and cost $335/night. The biggest issue however was the periodic sewage smell hidden by scented bleach. It seems like they have a septic or plumbing issue. Also, water pressure is non-existent. I would not stay here again. Nice view of harbor though.

L B.

Yelp
Ok. Here we go. Tried the Tavern downstairs ( Sushi restaurant upstairs ). Place is not upscale? It is basically a pub. The menu is high-priced. All food cold...calamari, FF, clam chowder. All cold. Very disappointed, spent 400 for 4 people, 2 drinks each. 1 of us got a burger, 1 of us got 2 orders of shrimp cocktail, 1 lobster roll. Nothing impressive. Again, almost diner food, at best. Employees dressed in backwards baseball caps, crumby tshirts...absolutely no dress code. We were first seated in the back room, absolutely no atmosphere, dark and dingy and looked unfinished. Requested a better, brighter table up front ( originally told us was all reserved ) but moved to one of those tables. Tables were supposed to be all reserved as told earlier, but the entire time tables were empty. Even the house Wine, Cabernet, was acidic and awful. One of us ordered black label scotch, waiter came back and said bar has no black, just red, but went upstairs to the sushi bar for a new bottle. Nope, no black. Won't be back, I suggest you pass.

Josh H.

Yelp
Wow this was absurd. Reviews of this place are spot-on. Rude/unprofessional/untrained staff. Was honestly entertaining to see how things continued to go wrong throughout the meal

Roger L.

Yelp
"Weakfish" restaurant - decent sushi, so so ramen with adequate service on a weeknight (July 21). Unfortunately, we were party of 7 which was too big to dine on the terrace. The interior noise level (probably intentional) is so loud that even the waiter couldn't hear to take our orders. Noah from Greenport "Noahs" runs the dining at the Chequit and am not sure who he isn aiming to attract on Shelter Island. Never again.
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Hanna M.

Yelp
remarkably bad food... serving cooked "hamachi" should be a crime. service took forever. whoever cooked this has never had authentic asian food in their life. a travesty, particularly for the price tag. do yourself a favor and order pizza instead, your wallet and taste buds will thank you.
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Victoria A.

Yelp
Perfect get away spot. Fresh breakfast, pleasant, kind staff, clean rooms, adorable decor-- there is so much to love! My boyfriend and I stayed for an overnight but should have planned a longer trip. It is so beautiful at this time of year on Shelter Island. The trees have changed color and the wineries are only a ferry and cab ride away. The front desk was so accommodating, they even checked in with us to have the room ready for our arrival. We got an upgraded room and were given directions whenever we wanted. Was a truly pleasant experience! I'm excited to come back with my girlfriends for a full weekend of wine and fun. Thank you for being such a lovely boutique hotel!

Tora M.

Yelp
The place just opened and we went by for dinner. The food was great - not a surprise since the Chef does an awesome job at his restaurant in Greenport. Dinner was great, the service was great, the sake was great - really couldn't ask for more. My fav dish was the Asian chicken entree - I'm going back for that again...

Sandra G.

Yelp
I didn't expect much from the look of the exterior but as soon as you walk you feel welcome and the interior looks beautiful and I can't stress this enough it's beautiful and stunning now I would recommend this restaurant if you're looking for something also there Asian food tastes divine the bar tenders are so kind and they are very patient.

Gulay L.

Yelp
went by to finally check out the new iteration of the Chequit.I am a local and have known this place all my life.We had lunch at the bar,and while the food Looked great ,the actual flavors were bland and poorly executed,and I was charged $32 for a simple mixed drink.the building looks great and I pray the food will get better,and the prices will be adjusted for our Island population.
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Rachael W.

Yelp
My boyfriend + I had such a wonderful weekend at the Chequit. Definitely the not sceney Shelter Island option (compared to sunset beach). If you're looking for a quiet, serene getaway, this is the place. Our room was in the cottage. The exterior of the cottage made us feel like we were at sleep-away camp, however, the interior felt nothing like that. Comfy plush white beds and a newly renovated bathroom - what more do you need? The website pictures are spot on - exactly what the room looks like. The staff couldn't be nicer or more accommodating. I think it would be helpful if management took each of them to visit each restaurant on the island so they can better direct people. No one told us about Vine st. when we asked about restaurants which we would have definitely went to had we known about it before our last night. No one told us to go into Greenport either. Instead we were recommended Sunset Beach which was definitely not what we were looking for and 18 Bay which was great and SALT which was really just bar food. Just a thought - staff was still amazing. Breakfast in the lobby was fantastic each day. You can sit on the porch and eat/drink your coffee for however long you like. They changed the egg dish and baked good each day and always had Greek yogurt with fruit. All in all - a perfect weekend getaway that really left me feeling like I was gone for weeks instead of only a few nights!
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Benjamin M.

Yelp
I love food but I lurve atmosphere! Raving about The Chequit is easy for me because it's got both. Let's start in the obvious place, the arrival: a late-afternoon promenade through the beautiful Greenport waterfront, past the historic piers, the window shops and the antique ferris wheel. Then you hop on the Shelter Island Ferry as a foot passenger: $2 each way. Now you're literally floating as the sun begins to dip, adding pastel colors to the coastlines you are sandwiched between. After the 5 minute ferry journey you climb a short but steep hill to earn the extended decadence in which you are about to indulge and the view that the hike affords. There are multiple floors and seating areas and a bar room. I recommend sitting as high as possible and, if not outside, then at least in view of the inlet. My family and family friends make the pilgrimage once a year for an annual celebration. I also took my ex-girlfriend here for Valentine's Day one year. The vive has never been short of elegant and the food has been consistently good. The menu may be a bit more ambitious than the result but fortunately the prices match the latter. Here's 6 words that make me happy as an East End restaurant-goer: local seafood, local produce, local wine! I like the food but it's the experience that keeps me coming back, forever ever - until I can't climb the hill.
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S L.

Yelp
My husband and I just came home from an enjoyable 3 day stay at The Chequit! We purchased a Living Social deal and stayed Sunday-Tuesday. Shelter Island is a quiet and relaxing place to go to for a small getaway and we really enjoyed our stay here! The room was a nice size, I do wish there were a little more counter/table space in the room and bathroom but it wasn't a big deal. They do let us know that the walls are 140 years old so at times we did hear the people over us but they eventually went to sleep. One really nice perk is a light breakfast (a baked good, yogurt parfait and coffee/tea) is included in your reservation, either in the lobby or breakfast in bed! It was very close to the north ferry but the island is so small that you can take the south ferry and still be there in no time. Pleasant experience all around!
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Al D.

Yelp
just visited this past weekend with my husband. even tho its just the beginning of the season, we found plenty to enjoy at this gorgeous hotel. the staff were incredibly kind and personable... we are vegan & they made sure we had vegan baked goods the next morning at their breakfast, plus chia pudding, fruit, toasts, trail mix, almond milk for coffee, etc.... the staff was also kind enough to heat our leftovers the next day and we ate in their very pretty lobby. it was too rainy to enjoy the deck but we still had fun. it feels like a B&B but slightly larger. the only criticism i have is that when i booked this, i had no idea the island was only accessible by ferry boat (no bridges). so leaving the island became kind of costly...$20 a day if you are doing a round trip. one day we went to Greenport, then the hotel, then to Sag Harbor and that was like $40 just to travel. kind of adds to the total cost. but I thought it was worth going to this wonderful sweet little place :)
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Jules H.

Yelp
We decided that ordering a drink around 11.59am is not breaking our rule of only drinking after 12noon. After all the drinks would arrive afternoon. When we asked for a menu, we were informed the kitchen had problems and we could not orders. When we advanced to the bar, they had a drink menu but no bar snacks. Grumpy start. They have a lovely sitting area outside and so we got comfortable and waited for our drinks and were amazed when they arrived in mason jars ... how hipster. After that we didn't see or hear from the staff for a good hour. I would say they forgot about us. We decided to ask for the bill and again were not attended to for a good 20min again, so to the bar we went to ask for our bill. They had problems with the credit card machine and it needed rebooting. Sigh. Not sure I would go there again, even though the drinks were great. The service was not.
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James K.

Yelp
It's hip, quiet and quaint. Add a star if you bike. That cuts down on the travel time to Sunset Beach which is really the only "cool" thing to do on Shelter Island. I've come out here twice for some long hilly bike rides. The hotel itself is in a nice little downtown. The verandas have views of a creek. The rooms do not have TVs. The steps are wooden and creeky. The hotel is old. It's the charm. The shower was clean. The room was clean. The staff very friendly and enthusiastic. We were walked to our room. The internet works great. It's a great spot for a telecommuter looking to bring the blood pressure down a few points. THIS IS NOT THE HILTON. It's mom and pop and charming. That being said, I found a pretty good deal for the room on Hotels Tonight.
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Tim R.

Yelp
Under new management and awesome. We were here during their first weekend after re-opening mid May 2015. The hotel is beautiful, clean, but still has that old school feeling. The staff was super nice, friendly, and helpful. The room was quaint, inviting, and comfortable. They hooked us up with a free bottle of wine and chocolates as we were celebrating our anniversary that weekend, much appreciated. They also offer free breakfast, either in bed or served at the lobby. We had it in the room and It was tasty. I can only imagine it will get even better once the restaurant opens downstairs. Thank you for a great and memorable stay Chequit Inn.
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W. S.

Yelp
Had a wonderful stay here with my wife. The Inn is beautiful and centrally located with a nice view of the bay. Julie and Rachel were great and made our stay so enjoyable that we plan on returning next month. They provided us with tips on the best places to visit on the island. The hot water bottle in each room was a very nice touch. We had dinner at the hotel's restaurant, " The Red Maple" which was very good. We had the pork tenderloin. Thank you Chequit Inn for making my bday weekend awesome...
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Mike H.

Yelp
Upon checking in to this delightful little Inn I was greeted by the most courteous and enthusiastic attendant I can imagine. He excitedly showed me around, and took my up to my room. A bit odd he did not offer to carry one of my bags though. My room itself was charming, however I found the air conditioning not be to working so it was 78 degrees in the room before I went down stairs to inquire about it. It turns out it was a simple fix, just needed to switch the hallway thermostat from heat to cool as the systems are linked. If that had been the only issue I would have been perfectly fine giving this place 5 stars. The big issue that I ran into is that the tiles on the bathroom floor were not grouted or secured to the floor. These are not the traditional bathroom tiles you might think of, but more stylish with sharp edges. If they were properly secured there would be no issue, and if it was a single tile it would have been forgivable. About 2 dozen tiles were coming up and stuck to my feet any time I walked on them. I even cut my foot on the broken one when I first discovered this. I reported the issue to the front desk and they apologize for the inconvenience. I would think that a boutique establishment such as this, would have at least asked if there was anything they could do to improve my stay giving the issue with the facility. I do know that they were fully booked, but having an attached restaurant free drink or a bottle of wine would not have gone amiss. Given how good everything else was I am inclined to give them a second chance. It is a very nice little inn.
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Angela D.

Yelp
I am a guest at the hotel. Decided to eat on site. The food was average. I have never seen green wild rice.It was lumpy. My husband ordered a medium steak, it was well done. The calamari was ok, portion was small. The shrimp cocktail was nice. The runner of food bumped into me and a kept moving over cause I was afraid he would again. I'm giving three stars because the service was ok ( a lil inconsistent)and the ambience is also nice. But I won't be eat here tomorrow. Celebrating my Anniversary. Somewhat disappointed. The one thing I can say is I really liked my room and it smelled great
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Ashley G.

Yelp
Let's just say I'm never going back. After sitting at the bar for 20 minutes i was actually thought i was invisible. I called out to the bartender 5x excuse me .. no response. It wasn't packed and they had 2 bartenders, they had enough to cover. Maybe "hi, I'll be right with you"? Nothing ! My husband and i picked up and left but not before i told the bartender why i was leaving, who responded "ok" and rolled her eyes. Then i stopped to tell the manager who said "sorry" and let us walk right out. Not coming back till they fire those horrible bartenders! Go to Shelter Island Tavern instead, they know how to treat their patrons
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Allison T.

Yelp
I have backpacked across Europe during college, staying in hostels only. I have traveled to South America on a $50/day budget. And yet, THIS hotel was the grossest place I've ever stayed. I only paid about $130/night which is a GREAT deal for memorial day weekend, but anything over $20/night at this place is highway robbery. My word of advice for you all: spend an extra $100 and stay somewhere else if you can! We didn't arrive until 10pm on a Friday, and upon walking in, we were directed via paper directions, to go downstairs to the bar to check-in. Fine. We were given keys to our room on the bottom floor of the 'Summer Cottage.' The room was about 10'x10' with one double bed taking up pretty much the whole thing. No headboard. Mildew on the lampshades. Rust on the A/C. (There IS an air conditioner though, that's where the 1 star comes in). Walls are so thin, I heard my neighbor snoring all night. I don't mind 'outdated,' but this place is beyond that. I'm really not sure how they even pass inspection. The entire place reeks of mildew. It just all needs to be ripped up and completely re-done. In 30 years of travel and hotels, I have never felt the need to voice a public complaint until now. Do. not. stay. here.
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Heather S.

Yelp
Something about this place reminds me of the few months after I finished college when I had a job as a server at a pretentious Yacht Club on the North Shore of Long Island. However, there is nothing pretentious about Chequit. Good beer on tap (Blue Point, Harbor, etc), friendly bartenders, plenty of indoor/outdoor seating and to top it off live music. The couple of times I've been to this Shelter Island hang out I've had a great time. I particularly enjoy that it never gets unbearably loud so you're still able to hold a conversation. ---- I wish the bathroom stalls had doors. I'm not a fan of the whole shower curtain thing that they've got going on.
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Pauline F.

Yelp
We were guests at The Chequit one of the first weekends it was re-openned. We felt very welcomed when we first arrived and were shown to our renovated room. The room itself was a little bare (no TV, drawers, seating other than one table chair and bed), but it had everything we needed for our one night stay. We took advantage of the complimentary wine hour hosted that evening and sat on the sun porch to enjoy the nice weather. (I believe it was their last weekend of it being 'complimentary'). They offer free breakfast, either in bed or served at the lobby. It was delicious and again a perfect opportunity to sit on the wonderful porch. The staff was great and I would definitely recommend The Chequit.
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Dennis U.

Yelp
After driving past the Chequit for many years we finally were near it around lunch time and hungry so we stopped. Lunch on the patio seemed like a good idea on a delightful afternoon so it was ideal. I was not disappointed. A glass of white wine and some grilled shrimp hit the spot. The wine selection was good , service was pleasant. Everything combined to make it a thoroughly delightful experience. I'm sure I'll time my cross Shelter Island trips to stop here again..
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Rupert N.

Yelp
This is by far best hotel in both Greenport and Shelter Island area. We have stayed in most around North Fork. Jason is unbelievable and will go to great lengths to make sure you're comfortable. This is really a 5 Star inn! We loved the wine by the fire at Sunset. Our King Deluxe room was HUGE... and the best... TOO comfy (almost). Every detail is perfection. The SERVICE is what really sets this place apart. THEY CARE and THAT is what matters most. BOOK NOW!
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Isadora S.

Yelp
This hotel, bar and restaurant are just divine! This place has all that you need to have a beautiful relaxing and restorative Long Island beach time. The staff is super sweet, the food is amazing and the overall vibe is " relax and enjoy". We loved the rooms and everything was modern, classy and clean. Food and wine are superb! Bravo! Also it's so close to all that you might need should you want to explore ;)