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The Chequit

23 Grand Avenue, Shelter Island Heights, Shelter Island, NY 11965
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The Chequit
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54 Reviews from our TripAdvisor Community

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London, United Kingdom
Level Contributor
28 reviews
28 hotel reviews
common_n_hotel_reviews_1bd8 41 helpful votes
3 of 5 stars Reviewed today NEW

We were looking forward to staying here - we saw several articles about it and the pictures looked gorgeous. We know shelter island but always go in the summer so are able to stay at the sunset beach hotel but as this shuts outside summer season we tried the Chequit. It is a beautiful old house in the centre of... More 

Helpful?
Thank MrsMuirdown
1 review
5 of 5 stars Reviewed 2 days ago NEW

First time staying here and visiting Shelter Island, and after our stay, we will definitely be back. The Chequit was beautiful. Great staff, very cute rooms and a great location. Only a quick walk to the ferry. Definitely a place to check out. And we are looking forward to head back!

Helpful?
Thank Nicole S
Rachel M, House Manager at The Chequit, responded to this review

Hi Nicole S, Thank you for your kind commendations! We appreciate your recognition of our efforts to provide a wonderful and memorable stay to each and every guest who walks through the doors of The Chequit. We hope to have the chance to see you again in the near future! More 

Sydney
Level Contributor
6 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 3 days ago NEW

What an amazing experience at the Chequit! We had a wonderful weekend, totally spoilt by the warmest and most attentive staff, they treated us like family from the moment we arrived. Our room was just gorgeous, beautifully designed and we hated leaving the bed in the morning, it was like sleeping on a cloud! However, the delicious, bountiful home made... More 

Helpful?
Thank Helen L
Rachel M, House Manager at The Chequit, responded to this review

Hi Helen L, Thank you for your kind words about The Chequit and our team! We are thrilled to hear how much you enjoyed your stay as well as your experience at Red Maple. We hope to have the chance to host you again the next time you make it back from Sydney! More 

Boston, Massachusetts
Level Contributor
3 reviews
5 of 5 stars Reviewed 1 week ago

Had my first (of what will be many I'm sure!) trip out to Shelter Island and The Chequit recently and I'm in love! The property staff were all wonderful and helped make my stay perfect - even during Blizzard Jonas! The bed was amazing (almost didn't want to get up!) and the food - even better! The location (right up... More 

Helpful?
Thank Chris H
Rachel M, House Manager at The Chequit, responded to this review

Hi Chris H, We are so happy that you chose The Chequit to host your first trip to Shelter Island! I agree, our custom-made pillow top mattresses provide the perfect nights rest! We pride ourselves on excellent service and I'm so glad you enjoyed your weekend even with Jonas! We look forward to welcoming you back to The Chequit soon! More 

hingham masssachusetts
Level Contributor
20 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 18 helpful votes
5 of 5 stars Reviewed 1 week ago

What a wonderful place to really get away from it all! I felt as though I had stepped back in time. Such a beautiful restoration of an old beauty! Welcoming from the moment we arrived on the big wooden front porch. The meeting area with a glowing fire and big comfortable seating was calling to sit, relax and have a... More 

Helpful?
Thank janetfrommass
Rachel M, House Manager at The Chequit, responded to this review

Dear Janetfrommass, Thank you for your kind commendations! I'm so glad you liked our newly renovated spaces, it was a labor of love to bring The Chequit back to her former glory while still maintaining that historic charm! I'm thrilled to hear that you enjoyed our restaurant Red Maple. We look forward to hosting you again soon for another winter... More 

New York City, New York
Level Contributor
44 reviews
44 hotel reviews
common_n_hotel_reviews_1bd8 86 helpful votes
4 of 5 stars Reviewed December 27, 2015 via mobile

This will bring you back to your camping days. Uneven floors, low ceilings, tiny bathrooms, no elevators all lend to an authentic and rustic charm. We laughed a lot and had a great time on shelter island and enjoyed visiting sunset beach. The area is beautiful but the hotel itself doesn't have much going on with the exception of the... More 

Helpful?
1 Thank LadyBren85
Rachel M, House Manager at The Chequit, responded to this review

Thank you for taking the time to share your feedback with us. We always strive for our guests to leave with a positive and memorable experience. I am glad to hear that you enjoyed your dining experience at our restaurant, Red Maple. The Chequit offers a variety of room types with different layouts. Please feel free to contact me directly... More 

New York City, New York
1 review
5 of 5 stars Reviewed November 17, 2015

The Chequit was such a lovely getaway from NYC to experience Fall. I've only every been to Shelter Island in the Summer before however this time around I experienced a new warm, local feel to the Island and The Chequit was the epicenter of this! Before checking in, we had an email from Julie (one of the Managers) with some... More 

Helpful?
Thank Rowan H
Rachel M, House Manager at The Chequit, responded to this review

Hi Rowan H, Thank you so much for taking the time to leave this review. I am thrilled to hear you had such a relaxing stay, it is easy to forget about the real world once you arrive at The Chequit! We are loving the fall season here on Shelter Island and the North Fork with the wineries and farm... More 

Lebanon, Pennsylvania
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed October 30, 2015

Lovely restored Inn on Shelter Island! We selected the Chequit Inn as a waypoint onto Newport. What we didn't know - is that we should have made it a several day stay. Beautiful environment on the porch, in the dining room and the grand common room (complete with piano). It was tranquil, charming and an unexpected treat. The service was... More 

Helpful?
Thank Sally M
Rachel M, House Manager at The Chequit, responded to this review

Thank you so much for taking the time to leave this review. I am thrilled to hear that you had such a special stay here at The Chequit! I'm so glad you enjoyed the new design, front porch and most importantly our staff. We look forward to welcoming you back soon for an extended stay! More 

Pike
Level Contributor
32 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 13 helpful votes
4 of 5 stars Reviewed October 18, 2015 via mobile

While the Inn is newly renovated, it missed the mark on some basic room amenities. The modern, minimalistic decor is nice, but there was no place to put a suitcase. The rooms are small and only allows for one chair with a tiny round table. The driftwood ladder looks cute, but is non-functional. Perhaps the space could allow for a... More 

Helpful?
1 Thank Patricia B
Rachel M, House Manager at The Chequit, responded to this review

Thank you for taking the time to share your feedback with us. We always strive for our guests to leave with a positive and memorable experience. I am glad to hear that you enjoyed the newly renovated spaces as well as our complimentary breakfast (with a daily changing menu featuring fresh and local ingredients)! The Chequit offers a variety of... More 

Level Contributor
33 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
5 of 5 stars Reviewed October 15, 2015

The Chequit has figured prominently in my family history, and it is the only lodging I would consider when staying on Shelter Island. I have stayed here multiple times over the years, and have always been pleased that this 140-year-old hotel has been lovingly maintained. Recently they have done a top-to-bottom remodel, which has resulted in a very tasteful update... More 

Helpful?
Thank mossyfy
Rachel M, Manager at The Chequit, responded to this review

Thank you for taking the time to share your feedback. We are so thrilled you enjoyed your stay! The renovation was a labor of love to keep the historic charm of the building but also add some modern amenities. It was lovely meeting you and learning of your family history not only at the Chequit but on Shelter Island. We... More 

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