The Chequit Inn

A dear friend suggested we stay here as a little get away from the city and it definitely was a great suggestion. From the moment we parked (thanks for the welcome Jenny!) to the minute we left, we felt like family. We were welcomed by a bottle of bubbly (thanks Rachel!) and a nice clean spacious room. Our 5 month old daughter appreciated the warm living room/​lounge area (calmed her down when she got a little anxious) and we appreciated being able to get fancy gourmet ‘take out’ from the Red Maple restaurant. Lovely accommodating accommodations and a cozy winter get away.

Had a wonderful three night stay at The Chequit! Lovely inn with delicious breakfast spread, attentive staff and beautiful accommodations. We loved enjoying our breakfast on the porch and reading the newspaper before heading out for our day’s adventures! Perfectly situated to enjoy all that Shelter Island has to offer!

We loved the inn. Clean and comfortable room! The bed, pillows and comforter were perfect. The morning breakfast was plentiful and delicious. We will definatly go back.

Great place in Shelter Island for dinner and/​or drinks. Menu is on the pricey side but the food was definitely worth it. Enjoyed a perfectly made Margarita and the Atlantic Cod with green beans + potatoes. Hostess, waitress, and bartenders were all very friendly and accommodating.

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!

A beautiful, incredibly charming inn (and easy walk up the road from the ferry). The service and accommodations are first-​rate. The staff takes the time to know your name. Perfect weekend getaway. You’ll see how this is an anchor in the Heights community.
Plan to relax and tune out and take note of your beautiful surroundings. It was my first time to SI and I was glad I did just that!
Great in-​room toiletries, rain shower, on-​site Jack’s Stir Brew café (delicious), FREE WiFi, a/​c a plenty and an extremely cozy and comfy King bed (no TV, don’t need it!).
The complimentary gourmet breakfast will knock your socks off! Be prepared to ENJOY every bite and sip your coffee with a newspaper on the porch. Still dreaming about the chia pudding (breakfast is different each day and it’s not a full meal but generous enough to satiate before lunch).
Be sure to rent a bike down the road at the gas station and RIDE all over the island! Across the street from rental is a wonderful upscale food shop & market, Marie Eiffel, which makes it easy to get great snacks and pack a lunch. Stars Café is another spot next to the inn for coffee, lunch or other food to-​go. Next door to the inn is a sweet, old-​timey pharmacy and soda fountain for pretty much anything you might need.
The Inn’s restaurant, Red Maple is the place to dine (the locals are ON IT). Dory’s for fresh lobster, Thursday $ 20 deal) and Sweet Tomato’s for delish Italian.
Seems to be kid-​friendly but this is a quiet property and no place for screaming children or people who want to party. A non-​denominational church is a short walk and they host Sunday service outside on the lawn in its community square in summer, I believe.
There’s a reason why the NY Times and top travel writers are falling in love with The Chequit which is how I learned of the inn (see their Instagram for the media posts and great pics). I was thrilled that what I experienced matched the press articles (not always the case).
I plan to return in the fall. I bet the island is gorgeous when the leaves change.
Thank you Chequit staff!

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!

This establishment has an outright predatory cancellation policy. Business necessitated that I cancel my anniversary stay, and I called WITHIN 24 HRs of having made the reservation. They basically told me to GO F$*K myself and that they were keeping my deposit, as that’s their policy. Thanks for doing what I consider to be stealing my money and ruining my anniversary. What a terrible place and business, IMO.

We were actually the second guests to check in at this newly renovated inn on beautiful Shelter Island. There were some opening weekend issues that spoke as much to the craftsmanship of the contractors doing the renovations as it did to the management for not inspecting the touch points more closely. The real test of customer service is how management reacts when things inevitably go wrong. That’s where the staff here stands out. They were great. They addressed every issue as well as they could and were over the top attentive. This will be a great place in a few weeks easily rating another star. Will definitely be back!

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.

Under new ownership, they are off to a good start. Raw bar this weekend was really great. I’m hoping plastic cutlery, plates and glasses were just because it was a soft opening? The table set up outside with staff shucking oysters was cool, would love that to happen all summer. Seafood was fresh and delicious and yummy mignonette and sauces as well.
We had a peek at the interiors, it’s an enormous improvement albeit a little cluttered and some unfortunate choices in lighting. Lace curtains on the upper porch have to go. Guys​.seri​ously​.no​.no​.no.
We are highly anticipating the opening of the bar and restaurant…

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.

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.

Don’t waste your time with the restaurant. We went with 3 couples and we will never go back. I sat down and immediately the chair leg broke and I found myself on the floor. Sadly only the waiter came out to see if I was ok. The waiter came back later and said that they will comp me a drink. At 58 I don’t bounce well anymore and I did get bruised. You would think a manager or the owner would come out, but they didn’t. The replacement chair had a nail sticking out if the cushion — so they brought a third chair.
Let’s move on to the lobster dinner! I break off the tail only to find a black looking tar ball. I showed the waiter and he took the dinner back to the kitchen. The waiter came back with the dinner and said that they told him that sometimes the black is from what the lobster eats. Well this lobster must have been eating from an oil spill. Once again the cowards hid behind the young waiter and did not come out to our table. I asked the waiter and hostess if they would eat a lobster like the one I was showing them, and they both said no way with a disgusted look on their face.
The rest of the food was below average and not worth the trip. The owners and managers dont care and it shows.

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.

Review for the bar only:
Chill vibe, strong drinks. And by strong drinks I mean you will get slightly more tipsy than you had previously planned. Or if you’re really good about driving they’ll make you a pretty Shirley Temple with a smirk. They have a pool table and darts, which makes for a great get-​together, or you can ask Rodondo to change the music up if you so wish to dance.
The Chequit Inn bar is one of the few places open late on the island, and it’s great if you just want to chill, but not spend your whole life savings away. Thumbs up!

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.

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.

When I’m vacationing or spending the day in Shelter Island I usually by pass The Chequit Inn for food because, well it’s a hotel and hotel food can be sub standard at times, but Chequit Inn really changes my outlook in this area.
I had the Turkey sandwich which was excellent as well as the Grilled Octopus salad. Wife had New England Clam Chowder and Goat Cheese Salad which were both equally as good. I ll be back for sure. Also service was great.

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.
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I wish the bathroom stalls had doors. I’m not a fan of the whole shower curtain thing that they’ve got going on.