Shelter Island Heights

£128-£145 – Shelter Island: Boutique 4-Star Hotel, Save 40%

The Chequit Inn
TOP 20 - Sells out quickly!
Karl Klockars
Deal Expert

Why We Love This Deal

This historic yet chic hotel with a B&B feel is "a lovingly restored Victorian beauty" (Telegraph UK) where members can save up to 40% on a stay that includes daily breakfast. 

"Idyllic ... offers a true escape from the congested sands of the Hamptons" ... Travel + Leisure

What's Included

  • £128 per night ... Sunday-Thursday in May 
  • £145 per night ... Sunday-Thursday in June 
  • Select April dates and a limited number of weekends are also discounted 

What You Need to Know

  • Price based on up to two guests sharing a room
  • These rates are refundable; book now and cancel later, if necessary
  • No resort fee 
  • Free Wi-Fi
  • Limited complimentary parking is available
  • Not pet-friendly; service animals only
  • For more details, see "Policies" and "Amenities" sections

Why We Love This Hotel

  • "Designed for dreamy summer jaunts to the East End" (Travel + Leisure) 
  • This boutique hotel sits in an 1870s-era hostelry; Frank Sinatra and Marilyn Monroe stayed here in the '40s and '50s
  • Enjoy a complimentary breakfast on the hotel's sweeping front porch overlooking the harbor


This charming boutique hotel offers a tranquil but stylish destination on an island that's "just minutes from the North and South Forks, yet ... it feels worlds away" (Conde Nast Traveler). Restored in 2015, the hotel feels like a B&B, with little extra touches like free use of beach umbrellas and towels as well as illustrated maps of the island. 

Stays here are focused on couples, with a variety of King rooms available. Freshly renovated furnishings feature restored hardwood floors, luxury bedding and rainfall showers and marble-accented bathrooms. Thanks to the Chequit's hilltop location, even though the property isn't on the shore, you can still get a view of the water from the guest-exclusive wraparound porch off the lobby. And like a B&B, complimentary breakfast is served daily in the lobby, but guests can opt to have coffee and pastries delivered to their rooms free of charge. 

Located at the eastern end of Long Island, Shelter Island is "the unassuming, quietly sophisticated alternative to the flash of the Hamptons" (Forbes). A full one-third of the island is a nature preserve, meaning there's plenty of bicycling, hiking and water activities like kayaking or paddleboarding -- or just hang out on one of the island's beaches or watch sailboats and yachts cruise in and out of the marinas. 



  • Bar
  • Newspaper / magazines
  • Restaurant
  • No pets allowed
  • Extra beds (fees apply)
  • 100% smoke-free
  • No elevator / lift


  • Concierge service
  • Room service (limited hours)

Room amenities

  • Air-conditioning
  • Central heating
  • Fridge


  • Complimentary Internet access
  • Complimentary Wi-Fi throughout


  • Hair-dryer
  • Separate shower
  • Luxury toiletries


  • Complimentary parking
  • Off-street parking


Check-in: Minimum age required to check in: 21.

The front desk is open from 8am to 7pm daily. Please call to arrange a check-in time, including for arrivals after 6pm.

Checkout: Standard Time is 11am.

Children and additional guests: Children 16 or under stay free of charge when using existing bedding.
Cot available upon request: free of charge.

Extra bedding (air mattress) available upon request: $50 USD plus tax, per night.
Cribs/ Pack 'n Play and air mattresses are based on availability.
Rates are based on double occupancy. Maximum occupancy for all rooms is 2 guests.

Cancellation: Cancellation policy & booking conditions vary by 'rate plan'. These will be displayed on the payment page after you have searched for your dates and selected a rate.

Additional details: All rates include a breakfast prepared fresh each morning, complimentary WiFi and on-site parking.

The restaurant (Red Maple) is closed seasonally from the beginning of November until the middle of May. 
The restaurant will reopen on May 18, 2019.

Roll in shower is available on request/per availability.

40% Off

£128 / night


When You Can Go

Options through June

Getting There

The Chequit is located on Shelter Island, which is approximately 3 hours east of New York City off of Long Island. Ferry transportation to the island is required. 

Have a Question? Contact Travelzoo.

Customer Service available Mon-Fri, 8am-6pm

Rates may vary by date, are subject to availability and are not guaranteed until your purchase is complete.

Please note: Some amenities and services may not be available in all rooms or may incur an additional charge. All prices stated have been verified at the time of publication and may vary at the discretion of the hotel.

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£128-£145 – Shelter Island: Boutique 4-Star Hotel, Save 40%

40% Off

£128 / night

Top 20 Deal — Sells Out Quickly