Shelter Island Hotels

Find the best Shelter Island hotel for your dates, by price or preference

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Look out for Shelter Island hotels with free cancellation or excellent ratings

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Prices may change – just add your dates for the best estimate. Note that prices are based on previous traveler searches and partner prices.
Prices may change – just add your dates for the best estimate. Note that prices are based on previous traveler searches and partner prices.
Taxes and fees not included
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Hotels in Shelter Island rated best by other travelers

Rated by travelers as the best in the city, these stays all get 5 stars for cleanliness, customer service and location.
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Luxury stay or budget getaway?

Whether you're after 5-star comfort or ease on your wallet, we do the searching so you can sleep easy during your stay in Shelter Island.

Fast facts

Sleep easy, armed with the stuff that's good to know before you go.
Highest-rated hotelThe Pridwin Hotel – 4.7

Your guide to finding the best hotels in Shelter Island, New York

To make the most of your time in Shelter Island, book a hotel that’s right for you. We’ve picked some of the city’s hottest hotels, from luxury to budget-friendly.

Best time to visit Shelter Island

When you're planning your vacation to Shelter Island, consider what you hope to do (or avoid) during your stay in terms of things like weather and price.

Where to stay in Shelter Island, New York

The most in-demand hotels are popular for a reason, and Skyscanner helps you score the right one at the best rate.

Popular hotels in Shelter Island

Here are some other great hotels in Shelter Island:

The 2.5-star Dering Harbor Inn provides a relaxing stay in the middle of Shelter Island, where you can enjoy its pool, gym, restaurant, and spa.

If you're looking for comfort and affordability, try the Shelter Island House. Its 3.5-star rating ensures exceptional value, and you can enjoy a range of amenities like the free Wi-Fi, fitness center, restaurant, and room service.

Rated as a 3-star hotel, The Pridwin Hotel and Cottages offers a wide range of amenities, such as a free Wi-Fi, Complimentary breakfast, fitness center and pet-friendly policy.

With a modern and comfortable design, the Sunset Beach is a 3-star hotel that provides free Wi-Fi, parking, 24-hour front desk, and air conditioning.

Things to do in Shelter Island

At the heart of the city, you can find well-known attractions and things to do like the Sylvester Manor Educational Farm. If you're a food lover, you'll find a smorgasbord of great places to eat, like Vine Street Cafe, Stars Cafe, Commander Cody's, The Islander, and The Pridwin Restaurant.

Finding cheap hotels in Shelter Island: FAQs

You can always cancel or amend your hotel reservation if you need to, but look out for hotels in Shelter Island with free cancellation or flexible booking options if you want to protect your money. Some hotels allow you to cancel and get your money back if your plans change.
Of course, the cheapest hotel deal we found within the next seven days is C$884 per night. If you need somewhere in the next 24 hours, we've found you somewhere to stay for C$1,819 per night.
The average price of a hotel during the week is C$1,018 per night, and the average price on weekends is C$969. Overall, it looks like the cheapest day to stay in Shelter Island could be Wednesday.
We crunched some numbers on our calendar and found that Wednesday is the cheapest day to stay in Shelter Island, and the most expensive day seems to be Friday.
The average price of a 3-star hotel in Shelter Island is currently around C$1,014 per night, and the cheapest 3-star hotel we've found is C$489 per night.
Get your morning laps at The Pridwin Hotel, The Sagaponack, and Baron's Cove.