Title: 5 Stars Hotels in Dering Harbor, Shelter Island from CA $317 - Find Cheap Dering Harbor Hotels With 5 Stars | Expedia.ca [Dering Harbor Travel Guide](https://expedia.ca/Dering-Harbor.dx553248634998885605)[Hotels in Dering Harbor](https://expedia.ca/Dering-Harbor-Hotels.d553248634998885605.Travel-Guide-Hotels)[Vacation Rentals in Dering Harbor](https://expedia.ca/Dering-Harbor-Vacation-Rentals.d553248634998885605.Travel-Guide-VacationRentals)[Flights to Dering Harbor](https://expedia.ca/Cheap-Flights-To-Dering-Harbor.d553248634998885605.Travel-Guide-Flights)[Things to do in Dering Harbor](https://expedia.ca/Things-To-Do-In-Dering-Harbor.d553248634998885605.Travel-Guide-Activities)[Dering Harbor Car Rentals](https://expedia.ca/Car-Rentals-In-Dering-Harbor.d553248634998885605.Car-Rental-Guide)[Dering Harbor Vacation Packages](https://expedia.ca/Dering-Harbor.d553248634998885605.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Dering Harbor, Shelter Island from CA $317 - ![](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 Dering Harbor 5 Star Hotels Tonight [Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-12-23&endDate=2025-12-24&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-12-24&endDate=2025-12-25&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Dering Harbor 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 | Room amenity](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1d639007.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 (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](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon CA $516 CA $907 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.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-Dering-Harbor-Hotels.s50-0-d553248634998885605.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Dering-Harbor-Hotels.s50-0-d553248634998885605.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 Dering Harbor. ![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 $338 CA $388 total Jan 1 - Jan 2, 2026 includes taxes & fees 9.4/10 Exceptional! (341 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 $219 CA $317 total Dec 24 - Dec 25 includes taxes & fees 8.4/10 Very Good! (599 reviews) [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Canoe Place Inn and Cottages](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Canoe Place Inn and Cottages 239 E Montauk Hwy Hampton Bays NY [Get rates](https://expedia.ca/Hotel-Search?startDate=06%2F01%2F2026&endDate=07%2F01%2F2026&selected=83519458&PinnedHotelID=83519458&HadPinnedHotel=true®ionId=553248634998885605) 9.8/10 Exceptional! (60 reviews) [](https://expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information) Still don't see what you're looking for? [See all properties in Dering Harbor.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025®ionId=553248634998885605&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=24%2F12%2F2025&endDate=25%2F12%2F2025®ionId=553248634998885605&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025®ionId=553248634998885605&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025®ionId=553248634998885605&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025®ionId=553248634998885605&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025®ionId=553248634998885605&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. ## Top Dering Harbor Hotel Reviews ## Find out more about Dering Harbor Luxury is the name of the game at the best 5 Stars hotels in Dering Harbor. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Dering Harbor 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Dering Harbor hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Dering Harbor without giving up even an inch of quality. 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