$166-$189 – Shelter Island: Boutique 4-Star Hotel, Save 40%
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
- $166 per night ... Sunday-Thursday in May
- $189 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.
- Newspaper / magazines
- No pets allowed
- Extra beds (fees apply)
- 100% smoke-free
- No elevator / lift
- Concierge service
- Room service (limited hours)
- Central heating
- Complimentary Internet access
- Complimentary Wi-Fi throughout the hotel
- Separate shower
- Luxury toiletries
- Complimentary parking
- Off-street parking
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.
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 and under stay free of charge when using existing bedding. Extra bedding (air mattress) available upon request: $50 USD plus tax, per night.
Crib/Pack 'n Play available upon request: free of charge.
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.
Extra bedding (air mattress) available upon request: $50 USD plus tax, per night.
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.
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.
$166 / night
Have a Question? Contact Travelzoo.
Rates may vary by date, are subject to availability and are not guaranteed until your purchase is complete.
The room rates listed are for double occupancy per room unless otherwise stated and exclude tax recovery charges and service fees.
It is the responsibility of the hotel chain and/or the individual property to ensure the accuracy of the photos displayed. Travelzoo is not responsible for any inaccuracies in the photos.
*Unless otherwise stated, Travelzoo-exclusive extras are valid once per stay (based on two adults sharing). Value is an estimate based on double occupancy. Extras are only included with Member Rates and may not be available on all dates. Extras are non-transferable and have no cash value. Total value may vary depending on time of booking and availability. When included, breakfast may be limited to 2 guests per stay subject to hotel’s discretion. Other restrictions may apply; see our T&Cs for details.
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.