Title: The Best 5 Star Hotels in Eastern Shore, MD from $94 | Expedia.com [Eastern Shore Travel Guide](https://expedia.com/Eastern-Shore.dx6025644)[Hotels in Eastern Shore](https://expedia.com/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels)[Vacation Rentals in Eastern Shore](https://expedia.com/Eastern-Shore-Vacation-Rentals.d6025644.Travel-Guide-VacationRentals)[Flights to Eastern Shore](https://expedia.com/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)[Things to do in Eastern Shore](https://expedia.com/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities)[Car Rentals in Eastern Shore](https://expedia.com/Car-Rentals-In-Eastern-Shore.d6025644.Car-Rental-Guide)[Eastern Shore Vacation Packages](https://expedia.com/Eastern-Shore.d6025644.Destination-Travel-Guides) ![Long Wharf Park](https://images.trvl-media.com/place/6286116/d4aad82a-b6ac-4cb6-992a-8f51658bb937.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6286116/d4aad82a-b6ac-4cb6-992a-8f51658bb937.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/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 [Mar 3 - Mar 4](https://www.expedia.com/Hotel-Search?regionId=6025644&startDate=2026-03-03&endDate=2026-03-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 4 - Mar 5](https://www.expedia.com/Hotel-Search?regionId=6025644&startDate=2026-03-04&endDate=2026-03-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=6025644&startDate=2026-03-06&endDate=2026-03-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6025644&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Eastern Shore 5-star hotels ![Premium bedding, down comforters, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/4ea15d12.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) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/6a6b34d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Perry Cabin [](https://www.expedia.com/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) Downtown St. Michaels 9.6/10 Exceptional (374 reviews) "Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph $371 nightly $408 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/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.com/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.com/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 $211 nightly $240 total Mar 10 - Mar 11 Total with taxes and fees 8.8/10 Excellent! (1,001 reviews) [](https://expedia.com/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 $124 nightly $139 total Mar 10 - Mar 11 Total with taxes and fees 8.8/10 Excellent! (1,350 reviews) [](https://expedia.com/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 $84 nightly $94 total Mar 8 - Mar 9 Total with taxes and fees 9/10 Wonderful! (1,004 reviews) [](https://expedia.com/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.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F4%2F2026&endDate=3%2F5%2F2026®ionId=6025644&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F4%2F2026&endDate=3%2F5%2F2026®ionId=6025644&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F4%2F2026&endDate=3%2F5%2F2026®ionId=6025644&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F4%2F2026&endDate=3%2F5%2F2026®ionId=6025644&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F4%2F2026&endDate=3%2F5%2F2026®ionId=6025644&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F4%2F2026&endDate=3%2F5%2F2026®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 savor 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.com/Hotel-Search?startDate=2026-03-17&endDate=2026-03-18&adults=2®ionId=6025644) ![Long Wharf Park](https://images.trvl-media.com/place/6286116/d4aad82a-b6ac-4cb6-992a-8f51658bb937.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Eastern Shore Hotel Reviews ## Find out more about Eastern Shore You enjoy the finer things in life, both at home and on vacation. Add further luxury on your next trip to Eastern Shore by treating yourself to the best of the best when it comes to accommodation. It's an ideal pairing. There's no reason to delay a getaway to Eastern Shore any longer. You'll join the multitudes of vacationers who have made Eastern Shore so fashionable in the last year. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Eastern Shore and indulge in the finer things in life for a while. ### Get a Great Deal on 5-Star Hotels in Eastern Shore You'll have a fantastic time at one of these 5-star hotels. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. How do you want to relax? A mud wrap treatment that will leave you feeling outstanding? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A deep-tissue massage to help your cares fall away? Can't wait to get outside? We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Eastern Shore are the perfect place to relax after an exciting day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs. ### Your Getaway Starts Today Numerous visitors make Eastern Shore the place to vacation. Why not join their ranks? If you've been dreaming about a vacation set here, then go ahead and book it. A surge in interest means these great hotel rooms will go quickly. It's time to plan your next great escape. Opt for one of our Eastern Shore 5-star hotels today and decompress in total tranquility tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Eastern Shore? > - Search for the lowest price per night from $94 ### What makes a hotel 5 stars in Eastern Shore? ### Are there any 5-star all-inclusive resorts in Eastern Shore? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Talbot Massage ](https://www.expedia.com/Talbot-Massage-Hotels.0-l553248621555566157-0.Travel-Guide-Filter-Hotels) - [Hotels near Easton Cycle and Sport ](https://www.expedia.com/Easton-Cycle-And-Sport-Hotels.0-l553248621532662348-0.Travel-Guide-Filter-Hotels) - [Easton Hotels ](https://www.expedia.com/Easton-Hotels.d7120.Travel-Guide-Hotels) - [4 Star Hotels in Easton ](https://www.expedia.com/4Star-Easton-Hotels.s40-0-d7120.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Easton ](https://www.expedia.com/5Star-Easton-Hotels.s50-0-d7120.Travel-Guide-Filter-Hotels) - 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