Title: 5 Stars Hotels in Shelter Island Heights, New York from CA $305 - Find Cheap Shelter Island Heights Hotels With 5 Stars | Expedia.ca [Shelter Island Heights Travel Guide](https://expedia.ca/Shelter-Island-Heights.dx183716)[Hotels in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)[Flights to Shelter Island Heights](https://expedia.ca/Cheap-Flights-To-Shelter-Island-Heights.d183716.Travel-Guide-Flights)[Things to do in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)[Shelter Island Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide)[Shelter Island Heights Vacation Packages](https://expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides) ![View from the back patio of The Dory Restaurant on Shelter Island, NY #shelterisland #reflections #silence #nature](https://images.trvl-media.com/place/183716/85195975-446e-456c-ac70-fc32257fab0e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Erisa Dilo # 5 Stars Hotels in Shelter Island Heights, New York from CA $305 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Shelter Island Heights 5 Star Hotels Tonight [Jan 5 - Jan 6](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-05&endDate=2026-01-06&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-06&endDate=2026-01-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-09&endDate=2026-01-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-16&endDate=2026-01-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island Heights 5-star hotels ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1f2aee03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/f6e6bd4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Living area](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1fbed560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mill House Inn [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) Pantigo Road Historic District 9.0/10 Wonderful (76) "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](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon CA $343 CA $431 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![House | Outdoor pool](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/23f4590c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Front of property](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/61df3ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Gazebo](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/de3513ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/a4e472c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Newmark Holiday home 7 BestStayz.1 [](https://www.expedia.ca/Sagaponack-Hotels-Casa-Newmark-Holiday-Home-7-BestStayz1.h32411044.Hotel-Information) Sagaponack [](https://www.expedia.ca/Sagaponack-Hotels-Casa-Newmark-Holiday-Home-7-BestStayz1.h32411044.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Shelter-Island-Heights-Hotels.s50-0-d183716.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Shelter-Island-Heights-Hotels.s50-0-d183716.Travel-Guide-Filter-Hotels) ## 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](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Gurney's Montauk Resort & Seawater Spa 290 Old Montauk Highway Montauk NY CA $455 CA $624 total Feb 5 - Feb 6 includes taxes & fees 8.2/10 Very Good! (710 reviews) [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Madison Beach Hotel 94 West Wharf Road Madison CT CA $337 CA $387 total Feb 5 - Feb 6 includes taxes & fees 9.4/10 Exceptional! (342 reviews) [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sound View Greenport 58775 County Rd 48 Greenport NY CA $232 CA $305 total Feb 4 - Feb 5 includes taxes & fees 8.4/10 Very Good! (602 reviews) [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Still don't see what you're looking for? [See all properties in Shelter Island Heights.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=183716&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=183716&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=183716&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=183716&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=183716&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=183716&star=50&star=50&amenities=WATER_PARK) 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](https://www.expedia.ca/Hotel-Search?startDate=2026-01-19&endDate=2026-01-20&adults=2®ionId=183716) ![View of Dering Harbor](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=650&h=652&p=1&q=high) Photo by Brian V. Rowe ## Top Shelter Island Heights Hotel Reviews ## Find out more about Shelter Island Heights ## Five Star Hotels in Shelter Island Heights There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Shelter Island Heights so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Shelter Island Heights and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Shelter Island Heights Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Shelter Island Heights The results are in, and Shelter Island Heights 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Shelter Island Heights! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Shelter Island Heights today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Shelter Island Heights? > - Search for the lowest price per night from CA $305 ### What makes a hotel 5 stars in Shelter Island Heights? ### Are there any 5-star all-inclusive resorts in Shelter Island Heights? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Hamptons ](https://www.expedia.ca/1Star-Hamptons-Hotels.s10-0-d6056452.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Plandome Heights ](https://www.expedia.ca/1Star-Plandome-Heights-Hotels.s10-0-d553248634998735582.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Lindenhurst ](https://www.expedia.ca/2Star-Lindenhurst-Hotels.s20-0-d183693.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Manorhaven ](https://www.expedia.ca/2Star-Manorhaven-Hotels.s20-0-d553248634998695724.Travel-Guide-Filter-Hotels) - 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