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Compare and book 5 Star hotels in Shelter Island Heights, New York

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Check availability on Shelter Island Heights 5 Star Hotels

Tonight
20 Dec - 21 Dec
Tomorrow
21 Dec - 22 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Shelter Island Heights 5-star hotels

Front of property – evening/night
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (75)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is 7.897.200 ₫
9.924.938 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Mill House Inn
House | Outdoor spa tub
Casa Newmark Holiday home 7 BestStayz.1

Casa Newmark Holiday home 7 BestStayz.1

Casa Newmark Holiday home 7 BestStayz.1
5.0 star property
Sagaponack
Casa Newmark Holiday home 7 BestStayz.1
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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 Heights.
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY
The price is 10.262.850 ₫ per night from 12 Jan to 13 Jan
10.262.850 ₫
14.070.368 ₫ total
12 Jan - 13 Jan 2026
includes taxes & fees
8.2/10 Very Good! (701 reviews)
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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 Heights

Victorian homes line the streets of this charming hamlet where you can rent bikes to explore the island's quiet beaches. Reserve a table at one of the waterfront restaurants for sunset views or take the short ferry to Greenport for more dining options.

See all hotels in Shelter Island Heights
View of Dering Harbor
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Top Shelter Island Heights Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Shelter Island Heights?
The amount you pay for a 5-star hotel in Shelter Island Heights depends on factors like when you plan to travel and the length of your stay. An insider tip for bagging the best deal? Use our pricing filters to compare all of the available options for your selected dates.

  • Search for the lowest price per night from 6.043.500 ₫

What makes a hotel 5 stars in Shelter Island Heights?
Outstanding guest service is integral to every 5-star hotel in Shelter Island Heights. From the minute you step through the door, staff cater to your every whim, whether offering luggage assistance and storage or providing a nightly turn-down service. Also, hotels must feature superior conveniences to obtain a 5-star rating. These can include deluxe baths, saunas or spas, swimming pools, fine dining kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Shelter Island Heights?
Expedia's filter tool is the easiest way to search for exactly what you want. Select "All inclusive" and "5-star" to see the most upscale properties in Shelter Island Heights where your meals, room, activities and entertainment are included in the price. At these stays, your holiday is pure extravagance from the moment you step foot in the lobby.