The Chequit Hotel Shelter Island Heights Exterior photoThe Chequit Hotel Shelter Island Heights Exterior photoThe Chequit Hotel Shelter Island Heights Exterior photo

The Chequit - Your Boutique Escape in Shelter Island Heights

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Check rooms and rates
From$826 /night
Check-in
12Jul
Check-out
13Jul
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

23 Grand Avenue, Shelter Island Heights, 11965
-
Near Crescent Beach
Perfect
9.0
8.6
/10
4.5
/5

The Chequit: A Victorian coastal retreat with 1940s glamour on Shelter Island

Accommodations & Ambiance

Lovingly renovated Victorian architecture greets guests at The Chequit, with views over Long Island Sound. Each air-conditioned room includes premium bedding and a private bathroom with complimentary toiletries. Family rooms are available with a daybed for children, and the thematic decor evokes the glamour of the 1940s throughout the property.

Dining & Local Flavors

The on-site restaurant, Red Maple, serves seasonal food with a bar for casual drinks. A complimentary breakfast is offered each morning, featuring fresh fruits, pastries, and homemade items. Guests can also visit the raw bar for local oysters and clams, or enjoy open-air dining on the expanded terrace during summer.

Amenities & Activities

A fleet of reconditioned vintage bicycles is available for complimentary use, allowing guests to explore the island at their own pace. The property includes a sun terrace and outdoor furniture for relaxation, as well as a shared lounge. Free WiFi and free on-site parking are provided, and the hotel accommodates pets upon request.

Location & Access

Situated near the North Ferry on Shelter Island, the hotel offers easy access to nearby attractions. Montauk is 34 km away, while East Hampton is 20 km from the property. The Chequit is close to spacious beaches, picturesque coves for family outings, and locations known for spectacular sunsets.

Activities & Local Scene

The hotel provides a quieter atmosphere compared to neighboring holiday towns, making it a distinct base for relaxation. Guests can attend local events or explore the natural beauty of the area. The Red Maple bar and restaurant also host DJ nights on Tuesdays, adding a low-key evening option for those who choose to stay in.

“Dining here is a genuine highlight, particularly for the fresh seafood, enjoyed best from a balcony overlooking the harbor. The recent renovations have modernized the rooms, and the staff consistently strikes a balance between attentiveness and genuine warmth, with particular commendation for Chris at the front desk. It stands as a rather remarkable and reliable choice for a getaway on the island.”
Hotel logo
James DavidEditor-in-Chief at Wonderfulhotels

Select your room type

The Chequit offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
  • Double Room Private Bathroom
    2 persons
    1 King-size bed
    Air conditioning
    Heating
  • Double Room Sea View
    2 persons
    1 King-size bed
    Air conditioning
    Heating
  • Standard Single Room
    2 persons
    1 King-size bed
Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!
July 2026 - July 2027
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Check-in/ Check-out

Facilities

The Chequit offers amenities for your comfortable stay and unforgettable experiences
Facilities: Perfect
10.0/10Review score

General

  • Non-smoking rooms
  • Wi-Fi
  • Parking
  • VIP check-in/ -out
  • Concierge desk
  • Pets allowed
  • Rooms/ Facilities for disabled
  • Luggage storage

Sports & Fitness

  • Golf course

Services

  • Housekeeping
  • Welcome drink

Dining

  • In-room breakfast
  • Bar/ Lounge area

Spa & Leisure

  • Sun terrace
  • Garden area

Room features

  • Air conditioning
  • Heating
  • Mini-bar
  • Terrace
  • Garden furniture

Bathroom

  • Free toiletries

Room decor

  • Parquet floor
Show more

The Chequit Location

23 Grand Avenue, Shelter Island Heights, 11965
Explore Shelter Island Heights
Explore Shelter Island
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Dering Harbor Marina
11 minutes' walk
Dering Harbor Marina features stunning views of the harbor and offers boat rentals, perfect for a maritime experience.
Shelter Island Country Club
10 minutes' walk
Shelter Island Country Club is a charming golf course known for its beautiful scenery and welcoming atmosphere.
Greenport Antique Carousel
5 minutes' drive
This historic carousel provides a nostalgic ride for all ages, with enchanting designs and a vibrant atmosphere.
Sylvester Manor
15 minutes' walk
Sylvester Manor is a historic estate with gardens and educational programs that offer a glimpse into the island's rich history.
Discover the local attractions near The Chequit
Uncover the nearby landmarks to enrich your stay near The Chequit and discover the unique history and culture of Shelter Island Heights.
Ideal for family outings: Greenport Antique Carousel
Great for scenic walks: Shelter Island
Perfect for immersive experiences: Sylvester Manor Educational Farm
Suited for historical exploration: The Village Blacksmith
Best for art lovers: VSOP Art + Design Projects
Ideal for informative visits: Fireboat Firefighter Museum
Works well for cultural appreciation: The South Street Gallery
Hiking at Mashomack Preserve
8 minutes' drive
Mashomack Preserve features numerous trails for hiking enthusiasts, showcasing diverse wildlife in a serene landscape.
Kayaking at Wades Beach
8 minutes' drive
Wades Beach offers kayaking rentals for those seeking adventure and a chance to explore the surrounding waters.
Red Maple
1 minute' walk
Red Maple serves contemporary American cuisine with locally sourced ingredients in a cozy setting. Reservations recommended.
Isola
2 minutes' walk
Isola offers Italian dishes with a focus on fresh seafood and homemade pasta, perfect for a romantic dinner.
The Flying Goat Restaurant
12 minutes' walk
This casual eatery is known for its farm-to-table philosophy and delicious comfort food in a laid-back ambiance.
Discover dining options near The Chequit
Explore the best nearby dining options that cater to various tastes and preferences near The Chequit.
Perfect for casual dining: Sweet Tomato's
Great for breakfast and brunch: Stars Cafe
Ideal for local cuisine: Isola
Suited for quick snacks: Shelter Island Heights Pharmacy
Best for gourmet selections: Marie Eiffel Market
Camera Obscura
25 minutes' walk
Camera Obscura provides a unique viewing experience of the surrounding environment, ideal for photography enthusiasts.
East End Seaport Maritime Museum
25 minutes' walk
This family-friendly museum showcases maritime history through exhibits, films, and events in an engaging environment.
Getting around
  • City Centre
    Shelter Island Heights 2 min  ·  400 ft
  • Airports
    Long Island MacArthur (ISP) 124 min  ·  51.3 mi
    Republic (FRG) 167 min  ·  69.0 mi
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Property information and rules
Check-in
from 16:00-21:00
Check-out
until 11 am
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in the entire hotel for free.
Pets
Pets are allowed on request.
Number of rooms:
36
Former name
Chequit Inn

Reviews and Ratings

Feedback about The Chequit from previous guests about their experience.
Review score
Based on 27 verified reviews
8.0 /10
Great
67 %
Recommend
Cleanliness
10.0/10
Comfort
10.0/10
Facilities
10.0/10
Location
10.0/10
Staff
10.0/10
Value for money
7.5/10
Pros
Historic Victorian architecture
Delicious entrees
Friendly staff
Centrally located
Beautiful grounds
Cons
Slow service
Inconsistent food
Broken amenities
Guest reviews
based on 1 reviews
9.0/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Open reviews

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