See all properties

The Chequit

Property class: 3

Choose dates to view prices

Photo gallery for The Chequit

An outdoor patio area with string lights, tables, chairs, and a fire pit. - The Chequit (Shelter Island Heights)
A large, white building with multiple windows and a prominent tree in the foreground. - The Chequit (Shelter Island Heights)
A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror. - The Chequit (Shelter Island Heights)
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony. - The Chequit (Shelter Island Heights)
A staircase with wooden balusters and a white wall. - The Chequit (Shelter Island Heights)
The Chequit provides amenities like a coffee shop/cafe and a restaurant. Stay connected with free in-room WiFi.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant

Room options

Available filters for rooms
Showing 10 of 10 rooms

View all photos for Summer House Standard

A neatly made bed with white linens and a patterned throw blanket. There are two bedside lamps with gold bases and white shades. A small table with a vase of flowers is visible to the left of the bed.

Summer House Standard

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

View all photos for Summer House Large

A bedroom with a bed, a chair, a table, a lamp, and a patterned rug.

Summer House Large

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

Summer Cottage Standard

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

Summer Cottage Suite

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed
  • Free WiFi

View all photos for Standard King

A neatly arranged bedroom with a large bed, a wooden chair, a small round table, and two hanging lamps.

Standard King

9.0 out of 10
Wonderful
(4 reviews)
  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

Deluxe King

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free WiFi

Washington Suite

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

View all photos for Superior King

A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

Superior King

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

View all photos for The Chequit Suite

A modern bathroom with a glass-enclosed shower, white tiled walls, and a toilet.

The Chequit Suite

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

Summer House Suite

  • Bay view
  • 18 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

About the neighborhood

Located near the beach, The Chequit is in The Heights, a neighborhood in Shelter Island Heights. Sylvester Manor and Camera Obscura are local landmarks, and the area's natural beauty can be seen at The Hamptons Beaches and Sunset Beach. Ready for a night out? Consider The Clubhouse Hamptons and The Watermill Center. Visit our Shelter Island Heights travel guide
Map
23 Grand Ave, Shelter Island Heights, NY, 11965

What's nearby

  • Shelter Island Country Club
    9 min walk - 0.5 miles
  • Sunset Beach
    3 min drive - 1.3 miles
  • Crescent Beach
    3 min drive - 1.3 miles
  • Sylvester Manor
    3 min drive - 1.8 miles
  • East End Seaport Maritime Museum
    20 min drive - 1.5 miles

Getting around

  • Greenport Station
    21 min drive
  • East Hampton, NY (HTO)
    43 min drive

Restaurants

  • Claudio’s Waterfront
    22 min drive
  • Goldberg’s Famous Bagels
    21 min drive
  • Aldo's
    21 min drive
  • Lucharitos
    21 min drive
  • Noah's
    21 min drive

Similar properties

Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio
The Harbor Front Inn
Greenport
  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
8.8 out of 10, Excellent, 644 reviews
The Harbor Front Inn
Compare similar properties

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free self parking on site

Food and drink

  • A coffee shop/cafe
  • A restaurant

Conveniences

  • Limited-hour front desk

Guest services

  • Housekeeping (on request)

Accessibility

  • No elevator

More

  • Smoking not allowed

Room amenities

Bedroom

  • Blackout drapes
  • Frette Italian sheets
  • Tempur-Pedic mattress

Bathroom

  • Private bathroom
  • Shower

More

  • Iron/ironing board on request

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: anytime
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

The front desk is open daily from 7:30 AM - 10:30 PM
Guests will receive an email within 72 hours before arrival with check-in instructions and key retrieval information; front desk staffed during limited hours
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours), key retrieval

Pets

Pets allowed for an extra charge of USD 250 per accommodation, per stay, plus a one-time cleaning fee of USD 250
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
2 total (up to 25 lbs per pet)
Pets cannot be left unattended

Children and extra beds

Children are welcome
Rollaway/extra beds are available for USD 25.00 per day
Cribs (infant beds) are not available

Important information

Optional extras

  • Pet fee: USD 250 per accommodation, per stay plus USD 250 one-time cleaning fee
  • Service animals are exempt from fees
  • Rollaway bed fee: USD 25.00 per day

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Noise-free guestrooms cannot be guaranteed
Safety features at this property include a smoke detector
Property Registration Number 86-3101878

We should mention

This property does not have elevators

Frequently asked questions

Is The Chequit pet-friendly?

Yes, this hotel allows cats and dogs (limit 2 total) with a maximum weight of up to 25 lbs per pet. There's a fee of USD 250 per accommodation, per stay. A cleaning fee of USD 250 also applies. Service animals are exempt from fees.

How much is parking?

Self parking is free at this property.

What time is check-in at The Chequit?

Check-in start time: 4:00 PM; Check-in end time: anytime.

What time is check-out at The Chequit?

Check-out is at 11:00 AM.

Where is The Chequit located?

Located in The Heights, this hotel is within 1 mi (2 km) of Shelter Island Country Club, Sunset Beach, and Crescent Beach. Sylvester Manor and East End Seaport Maritime Museum are also within 2 mi (3 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

The Chequit Reviews

9.2

Wonderful

9.6

Cleanliness

9.2

Amenities

9.0

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 41 out of 54 reviews
Rating 8 - Good. 7 out of 54 reviews
Rating 6 - Okay. 2 out of 54 reviews
Rating 4 - Poor. 2 out of 54 reviews
Rating 2 - Terrible. 2 out of 54 reviews

Reviews

Verified review

10/10 Excellent

Sharon

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
pretty and clean!
Stayed 4 nights in Aug 2026
Verified review

8/10 Good

Neal

Liked: Cleanliness, staff & service, property conditions & facilities
A cozy room with great pillows and quiet. Perfect little place.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

robin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fabulous stay .. staff amazing , customer service amazing will def come Back
Stayed 2 nights in Sep 2023
Verified review

10/10 Excellent

Beth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Chris, the front desk representative, was so helpful. He was kind and willing to help.
Stayed 1 night in Sep 2024
Verified review

10/10 Excellent

Javier

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Almost perfect

Overall a great experience. My only issue is that we were given room #2 -and while it’s a great room - due to its location on the first floor it can be noisy in the morning. There seems to be a supply closet right be the door and in the morning workers were getting supplies and talking. Also, the way that the room is set up when you open the front door to the room you can see right into the room and directly to the bed. The hotel was amenable in switching rooms for us if we wanted. Anyway, it was a very good experience and we would definitely be back if the opportunity presented itself.
Stayed 2 nights in Aug 2023
Verified review

10/10 Excellent

Catherine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We reserved one of the large suites and it was just fabulous. I can’t stand enough about the staff. They were incredible. You can’t beat the location. You can walk to everything. We had a wonderful weekend.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Kathleen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was great ! Wish we had been there when restaurant was open.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Kristin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Sharon

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
location!
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Always a sold stay on Shelter Island
Stayed 1 night in Aug 2025
Verified review

10/10 Excellent

Vanessa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Prefect place for a staycation
Stayed 1 night in Aug 2022
Verified review

8/10 Good

Maribeth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Room small but very functional, well decorated, bath modern, and very upscale. First night the attendant was wonderful. That was on the 18th. Next day, we had a leak at the shower because the molding on shower door was not working correctly, and the floor got wet. Staff was not really very responsive to that. Had a wonderful area for eating at the restaurant with nice fire pits, very nice with an overview of the water. Nice porch to be able to sit and read in the morning or many people were doing work. One annoyance was that one of the guests was having his phone on speaker while he had a business meeting and he spoke totally out loud, and was very distracting and basically rude. He should’ve taken that conversation elsewhere and taken a walk or gone back to his room. Staff did not feel that there was any need to say anything to him. “It’s a public space” Also, there was an area right near the parking lot that was right adjacent to the building that was totally mowed in full of weeds, that really would’ve been nice if it was cleared up. In all we would return, it was very pleasant otherwise. Nice view of the harbor small but nice. And located really conveniently right by the ferry.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Gabriele

Liked: Cleanliness, staff & service, property conditions & facilities
Property was amazing for our stay in Shelter Island
Stayed 1 night in Aug 2022
Verified review

10/10 Excellent

Aracely

Liked: Cleanliness
Everyone was amazing
Stayed 1 night in Aug 2025
Verified review

10/10 Excellent

maura

Liked: Cleanliness, amenities, property conditions & facilities
we loved it!
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Kirill

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very spacious room, great coffee, there is a pub downstairs
Stayed 1 night in Jun 2024
Verified review

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely beautiful! I really hope to be back there again soon!
Stayed 1 night in Aug 2024
Verified review

10/10 Excellent

Lucas

Excellent
Stayed 1 night in Nov 2024
Verified review

10/10 Excellent

mark

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wish they had full cable other than that highly recommended
Stayed 4 nights in Aug 2024
Verified review

10/10 Excellent

Charles

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
-
Stayed 1 night in Aug 2025
Verified review

6/10 Okay

Ken

Liked: Cleanliness, property conditions & facilities
The hotel was very clean , except for two half bottles of soda left in the room refrigerator , the room was so small there wasn't enough room for a chair so other than the bed no place to sit.
Stayed 2 nights in Jul 2024
Verified review

6/10 Okay

george

Liked: Cleanliness, staff & service
Disliked: Amenities, property conditions & facilities
We had a room with an old door adjoining the next room. You could hear right through it like it was made of paper. It was like sharing a room with a stranger. The stranger came back at two in the morning and kept us awake for 3 hours. For the money it hard to believe that they would subject their guests to it.
Stayed 3 nights in Sep 2023
Verified review

4/10 Poor

frederick

Disliked: Staff & service
I was either misquoted a price of $318.27 and was charged $407.05 on my credit, both of which were sent to my email on the Expedia website. As a vonsequence, I am requesting a refund of $88.78 to my credit card. Thank you.
Stayed 1 night in Aug 2023
Verified review

2/10 Terrible

Verified traveler

Disliked: Staff & service, property conditions & facilities, room comfort
Unfortunately did not meet my expectations for $362 a night. Very disappointed. Not even a chest of drawers or stand to hold your bag for your clothing. Nightstands were wood attached to the wall. No TV nor refrigerator. 2 bottles of water on the table but nothing to keep them cold. Locking the door does not seem secure because you can see the light from outside around the door. Parking lot did not exist because they are under construction. I would definitely not recommend this hotel.
Stayed 2 nights in Jul 2022
Verified review

10/10 Excellent

Gerardo

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Gran ubicación. Muy cómodo y muy bonito el hotel. Las habitaciones de muy buen tamaño. Muy agradable el hotel.
Stayed 2 nights in Aug 2026