United States
Shelter Island Heights
The Chequit
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Welcome to The Chequit – Shelter Island Heights

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Check rooms and rates
From826US$ /night
Check-in
26Oct2025Select date
Check-out
27Oct2025Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

23 Grand Ave, Shelter Island Heights, New York, United States, 11965
“"Shelter Island's charm and tranquility made my getaway lovely!"”view full review

The Chequit is a lovingly restored Victorian beauty with views over the Long Island Sound, inspired in spirit and style by the glamorous 1940s when Frank Sinatra and Marilyn Monroe reportedly stayed at this 4-star establishment. This once Methodist retreat nestling into the North Fork of Long Island offers a sun terrace, sea views, and remains something of a secret compared with the more crowded holiday towns of the nearby Hamptons.

Distinctive Room Options

All guestrooms at The Chequit feature comforts such as premium bedding and free WiFi. Suites include the Terrace Suite with its own roof terrace complete with love seat and claw-foot bath in the bedroom, while the six rooms in the Summer House are more simply furnished and more affordable.

Local Culinary Offerings

Red Maple restaurant serves a selection of small bites and traditional mains, including local Montauk fluke and root beer-glazed pork belly. The restaurant has an expansive terrace for open-air dining in summer and transforms into Mr Crook's Pub, a cosy British-style pub hosting trivia nights along with hearty food.

Breakfast and Cafés

Complimentary breakfast includes fruits, cereals, home-made muesli, freshly baked muffins, pastries, fresh juices, and tea and coffee served in the lobby and on the terrace. The White Hill Café sells picnic ingredients and hampers as well as coffees, juices, and snacks, while a raw bar offers local oysters and clams.

Island Exploration Amenities

A fleet of reconditioned vintage bikes are available for complimentary use to explore the island. The property features a shared lounge, shops, concierge services, gift shops/newsstands, and a fireplace in the lobby.

NYC Accessible Location

The Chequit is just two-and-a-half hours from New York City and a 10-minute ferry journey from Greenport on the north side or Sag Harbor to the south. The Long Island Rail Road also runs from New York's Penn Station, with the hotel located 85 km from Long Island MacArthur Airport.

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Select your room type

Choose from doubles, suites, or family rooms, many with breakfast, flexible cancellation, and promotional rates
Double Room Private Bathroom
Double Room Private Bathroom
2 persons
Shower
Heating
room details
Double Room Sea View
Double Room Sea View
2 persons
Shower
Heating
room details
Deluxe Double Room
Deluxe Double Room
2 persons
Large Double Room
Large Double Room
2 persons
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Price and Room Availability Calendar

Check availability and prices for your dates now!

Getting around

A guide to all available transportation options

City Centre
Shelter Island Heights100 m
Airports
Long Island MacArthur (ISP) 82.6 km
Republic (FRG) 111.1 km

Facilities

Boutique hotels design their amenities with your relaxation and unique travel experiences in mind
Excellent Sushi Experience
“I had the pleasure of dining at the restaurant recently, and the entire area has been revamped beautifully! I opted for some sushi, and the selection was very nice. I couldn't resist the martini rock shrimp tempura and a mix of rolls that included spicy tuna and shrimp tempura. Each bite was delicious, and the atmosphere was just fine with both indoor and outdoor seating. Can't wait to go back!” view full review
Luxurious Rain Shower
“The bathroom in my room was a true sanctuary! The rainfall glass shower was amazing, making my showering experience relaxing and refreshing. Plus, the luxury bath products were a lovely touch, adding to the overall charm of the room. It certainly felt more like a spa than just a bathroom.” view full review
Charming and Comfortable Room
“My room at The Chequit was simply charming! It was clean, comfortable, and felt very cozy. The bed was plush with top-of-the-line linens , made for restful nights. I found the ambient atmosphere perfect for unwinding, making my getaway truly relaxing.” view full review
Dog-Friendly Stay
“What I loved most was how cute the hotel was to my furry friend! I brought my 7-year-old Maltese with me, and the hotel staff was good, offering her treats whenever we passed by the front desk. The experience made our stay feel even more special. It was such a relief knowing she was welcome alongside us.” view full review

General

  • Wi-Fi
  • Parking
  • Pets allowed

Room features

  • Mini-bar

Bathroom

  • Free toiletries

Room decor

  • Parquet floor
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Location

23 Grand Ave, Shelter Island Heights, New York, United States, 11965
Map view
23 Grand Ave, Shelter Island Heights, New York, United States, 11965
City landmarks
Landmark
Dering Harbor Marina
900 m
Amusement Park
Greenport Antique Carousel
2.1 km
Landmark
Shelter Island Country Club
760 m
Landmark
Fireboat Firefighter Museum
2.0 km
Golf Course
Shelter Island Golf Course
760 m
Landmark
Congregation Tifereth Israel
2.1 km
Landmark
Sylvester Manor
1.2 km
Gallery
Nova Constellatio Gallery
2.3 km
Landmark
Camera Obscura
2.1 km
Landmark
East End Seaport Maritime Museum
2.4 km
Harbour
Greenport
2.2 km
Landmark
Railroad Museum of Long Island
2.5 km
Event hall
Sylvester Manor Educational Farm
2.6 km
Landmark
Sunset Beach
1.4 km
Beach
Crescent Beach
1.9 km
Landmark
Fire Fighter Ship New York
1.9 km
Island
Shelter Island
2.2 km
Museum
East End Seaport Museum and Marine Foundation
2.5 km
Market
The Gatehouse At Sylvester Manor
1.7 km
Landmark
Greenport Theatre
2.1 km
Landmark
Long Island Train Museam
1.9 km
Landmark
Beall & Bell
2.3 km
Museum
The Village Blacksmith
2.1 km
Gallery
VSOP Art + Design Projects
2.1 km
Landmark
watchtower
2.1 km
Landmark
Greenport Fire
2.1 km
Landmark
Shelter Island Whale's Tail
2.1 km
Landmark
Saint Agnes Roman Catholic Church
2.1 km
Gallery
The South Street Gallery
2.3 km
Nearby
Church
Our Lady of the Isle Church
570 m
Restaurants
Red Maple
20 m
23 Grand Ave
Isola
140 m
15 Grand Ave
Dory
350 m
185 N Ferry Rd
The Flying Goat Restaurant
950 m
26 Sunnyside Drive Shelter Island Country Club
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Check-in
26Oct2025Select date
Check-out
27Oct2025Select date
Rooms and Guests2 Guests, 1 Room
  • Overview
  • Rooms
  • Price calendar
  • Facilities
  • Location
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