Are there any 5-star vacation rentals in Shelter Island?

There are no 5-star vacation rentals in Shelter Island on our site, but there are some other highly rated options worth checking out. Search through our vacation rentals in Shelter Island to find the perfect place for your getaway.

Great shot of Sunset Beach on Shelter Island from our boat, before heading closer to anchor and swim in. A beautiful little slice of Southern France right here on Long Island Sound! If you get a chance, definitely check this place out.

Find 5 Star Hotels in Shelter Island, NY from SAR 1,647

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"Great experience at a wonderful property!"

SAR 4,690 total

includes taxes & fees

14 Jul - 15 Jul

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Shelter Island.

Montauk Yacht Club

32 Star Island Rd, Montauk, NY

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8.4/10 Very Good! (1,002 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Shelter Island

Escape to Shelter Island! Enjoy its island views, natural setting, and beaches.

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Shelter Island?

How much you pay for a 5-star hotel in Shelter Island depends on things like when you want to go and the length of your break. An insider tip for scoring an awesome deal? Use our pricing filters to check out the available options for your preferred dates.

Search for the lowest price per night from SAR 1,647

What makes a hotel 5 stars in Shelter Island?

In Shelter Island, a hotel must offer a certain amount of high-end conveniences to be designated 5 stars. These may include on-site gyms, spas and saunas, gourmet restaurants, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their guest-focused standard of service. You can expect things like in-room massages, nightly turn-down services and concierge services. Some may even offer special touches such as welcome gifts.

Are there any 5-star all-inclusive resorts in Shelter Island?

Our handy filters are the quickest way to search for exactly what you want. Check the "All inclusive" and "5-star" boxes to see the most upscale properties in Shelter Island where your accommodations, meals, entertainment and activities are included in the price. At these stays, your trip is pure leisure from the moment you arrive.