Title: The 10 Best 5 Star Hotels in Eastern Shore - 2025 Updated Prices | Expedia.co.uk [Eastern Shore Travel Guide](https://expedia.co.uk/Eastern-Shore.dx6025644)[Hotels in Eastern Shore](https://expedia.co.uk/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels)[Holiday Rentals in Eastern Shore](https://expedia.co.uk/Eastern-Shore-Holiday-Rentals.d6025644.Travel-Guide-HolidayRentals)[Flights to Eastern Shore](https://expedia.co.uk/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)[Things to do in Eastern Shore](https://expedia.co.uk/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities)[Eastern Shore Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Eastern-Shore.d6025644.Car-Hire-Guide)[Eastern Shore Holidays](https://expedia.co.uk/Eastern-Shore.d6025644.Holidays-City-Breaks) ![Long Wharf Park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253260-Eastern-Maryland.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Compare and book 5 Star hotels in Eastern Shore, Maryland ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Eastern Shore 5 Star Hotels Tonight [13 Oct - 14 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [14 Oct - 15 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastern Shore 5 Star Hotels ![Breakfast, lunch, dinner served; sea views ](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/6a6b34d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/3dd4d01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/2de6ebed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Perry Cabin St. Michaels 9.6/10 Exceptional (365) "Beautiful place to stay." £366 includes taxes & fees 12 Nov - 13 Nov [](https://www.expedia.co.uk/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Eastern-Shore-Hotels.s50-0-d6025644.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Eastern-Shore-Hotels.s50-0-d6025644.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 Eastern Shore. ![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency Chesapeake Bay 100 Heron Blvd, Cambridge, MD £198 19 Oct - 20 Oct includes taxes & fees 8.6/10 Excellent! (1,004 reviews) [](https://expedia.co.uk/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Hilton Ocean City Oceanfront Suites](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/502613d6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Ocean City Oceanfront Suites 3200 N Baltimore Ave, Ocean City, MD £95 2 Nov - 3 Nov includes taxes & fees 8.8/10 Excellent! (1,261 reviews) [](https://expedia.co.uk/Ocean-City-Hotels-Hilton-Ocean-City-Oceanfront-Suites.h27630.Hotel-Information) ![DoubleTree by Hilton Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/94fd6605_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Ocean City Oceanfront 3301 Atlantic Ave, Ocean City, MD £77 26 Oct - 27 Oct includes taxes & fees 8.8/10 Excellent! (1,006 reviews) [](https://expedia.co.uk/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) Still don't see what you're looking for? [See all properties in Eastern Shore.](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=6025644&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=6025644&star=50&star=50&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=6025644&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=6025644&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=6025644&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=6025644&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 Eastern Shore Beautiful beaches, fresh seafood, quaint local heritage and unforgettable outdoor adventures make the Maryland section of the Delmarva Peninsula the place to be. [See all hotels in Eastern Shore](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28&adults=2®ionId=6025644) ![Long Wharf Park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253260-Eastern-Maryland.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Eastern Shore Hotel Reviews ## Find out more about Eastern Shore ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Eastern Shore? > The amount you pay for a 5-star hotel in Eastern Shore depends on factors such as when you plan to travel and the length of your getaway. Our top tip for landing 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 £77 ### What makes a hotel 5 stars in Eastern Shore? > From high-end restaurants and fitness centres to swimming pools and premium bedding, the 5-star experience in Eastern Shore is all about comfort and luxury. But it calls for more than just upscale perks to earn a 5-star rating. Hotels must also offer superb guest-centric services like massage treatments, laundry and dry cleaning and 24-hour room service. ### Are there any 5-star all-inclusive resorts in Eastern Shore? > Use our filter tool to find a luxury escape in Eastern Shore where everything you need is included in the price. After your initial search, refine your results for hotels that have a 5-star rating and are categorised as "All inclusive." The main thing on the itinerary at these stays? 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