Title: 5 Stars Hotels in Eastern Shore, Maryland from CA $143 - Find Cheap Eastern Shore Hotels With 5 Stars | Expedia.ca [Eastern Shore Travel Guide](https://expedia.ca/Eastern-Shore.dx6025644)[Hotels in Eastern Shore](https://expedia.ca/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels)[Vacation Rentals in Eastern Shore](https://expedia.ca/Eastern-Shore-Vacation-Rentals.d6025644.Travel-Guide-VacationRentals)[Flights to Eastern Shore](https://expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)[Things to do in Eastern Shore](https://expedia.ca/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities)[Eastern Shore Car Rentals](https://expedia.ca/Car-Rentals-In-Eastern-Shore.d6025644.Car-Rental-Guide)[Eastern Shore Vacation Packages](https://expedia.ca/Eastern-Shore.d6025644.Destination-Travel-Guides) ![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) # 5 Stars Hotels in Eastern Shore, Maryland from CA $143 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-09-30&endDate=2025-10-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-01&endDate=2025-10-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastern Shore 5 Star Hotels ![Breakfast, lunch, dinner served; ocean views](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334.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) ![Suite, 1 Bedroom, Garden View | Garden view](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/b1a0ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, 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 (364) "Beautiful place to stay." CA $745 CA $902 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/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.ca/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.ca/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 CA $266 CA $368 total Oct 1 - Oct 2 includes taxes & fees 8.6/10 Excellent! (1,012 reviews) [](https://expedia.ca/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 CA $177 CA $197 total Oct 26 - Oct 27 includes taxes & fees 8.8/10 Excellent! (1,266 reviews) [](https://expedia.ca/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 CA $129 CA $143 total Oct 26 - Oct 27 includes taxes & fees 8.8/10 Excellent! (1,027 reviews) [](https://expedia.ca/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.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=6025644&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=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=6025644&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=6025644&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=6025644&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=6025644&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%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 Charming coastal towns and pristine beaches dot the Chesapeake Bay's eastern shoreline, inviting you to explore maritime history and savour fresh seafood. Kayak through serene marshlands, visit Assateague Island's wild ponies, or take a scenic drive to discover quaint antique shops and waterfront restaurants. [See all hotels in Eastern Shore](https://www.expedia.ca/Hotel-Search?startDate=2025-10-14&endDate=2025-10-15&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 ## Five Star Hotels in Eastern Shore 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 Eastern Shore 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 Eastern Shore and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Eastern Shore 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 Eastern Shore The results are in, and Eastern Shore 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 Eastern Shore! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Eastern Shore 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 Eastern Shore? > How much you pay for a 5-star hotel in Eastern Shore depends on factors such as when you plan to go and the length of your escape. Our insider tip for scoring an awesome deal? Use our pricing filters to compare all of the available accommodations for your selected dates. > > > > - Search for the lowest price per night from CA $143 ### What makes a hotel 5 stars in Eastern Shore? > Faultless guest service is the hallmark of every 5-star hotel in Eastern Shore. From the second you arrive, staff attend to your every whim, whether arranging customized tours or providing in-room massages. Additionally, hotels have to offer upscale conveniences to be entitled to a 5-star rating. These can include luxury toiletries, spas or saunas, swimming pools, gourmet kitchens and knowledgeable concierge. ### Are there any 5-star all-inclusive resorts in Eastern Shore? > Find an indulgent stay that includes your lodging, meals, bar and entertainment in Eastern Shore with our handy filter tool. Search for resorts rated 5 stars and select the "All inclusive" filter. Double-check what's included in the upfront price. 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