Title: 5 Stars Hotels in St. Michaels, Maryland from CA $156 - Find Cheap St. Michaels Hotels With 5 Stars | Expedia.ca [St. Michaels Travel Guide](https://expedia.ca/St-Michaels.dx5940)[Hotels in St. Michaels](https://expedia.ca/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)[Vacation Rentals in St. Michaels](https://expedia.ca/St-Michaels-Vacation-Rentals.d5940.Travel-Guide-VacationRentals)[Flights to St. Michaels](https://expedia.ca/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights)[St. Michaels Car Rentals](https://expedia.ca/Car-Rentals-In-St-Michaels.d5940.Car-Rental-Guide)[St. Michaels Vacation Packages](https://expedia.ca/St-Michaels.d5940.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/e708a2ddef7b36b18845a12b959447e3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in St. Michaels, Maryland from CA $156 - ![](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 St. Michaels 5 Star Hotels Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-11-03&endDate=2025-11-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-11-04&endDate=2025-11-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-11-14&endDate=2025-11-16&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top St. Michaels 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) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/6a6b34d6.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 (368) "Friendly and attentive staff, good cleaning services" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan CA $541 CA $655 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Horseback riding](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ad846553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/9273007e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, Bay View](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/aa3e4df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Studio Suite | Terrace/patio](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ed0e25a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate Tracys Landing 9.2/10 Wonderful (10) "The place was gorgeous. Very private and peaceful. Staff was great and i will definitely go back ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey [](https://www.expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![Dinner served](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/be8a1621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/82384fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/w264h344x4y2-b20fcf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/625fcac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at 202 Dover Easton 10/10 Exceptional (14) "We stayed in the French Room at the Inn at 202Dover in Easton, MD. We were welcomed by the manager, Vincent. The room was just as beautiful as it looked in the photos! The whole inn is a gem! The only thing I didn't end up trying was the hydrojet massage bathtub. There were directions in the guest book in the room but it just seemed too complicated for me. We also didn't use the steam shower, just had regular showers. We had dinner on the Friday night at the Inn and the food was delicious... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne [](https://www.expedia.ca/Easton-Hotels-Inn-At-202-Dover.h5308723.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-St-Michaels-Hotels.s50-0-d5940.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-St-Michaels-Hotels.s50-0-d5940.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 St. Michaels. ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Graduate by Hilton Annapolis 126 West St, Annapolis, MD CA $203 CA $232 total Nov 24 - Nov 25 includes taxes & fees 9.2/10 Wonderful! (1,024 reviews) [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Annapolis 210 Holiday Court, Annapolis, MD CA $137 CA $156 total Nov 9 - Nov 10 includes taxes & fees 8.6/10 Excellent! (1,018 reviews) [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![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 $223 CA $293 total Nov 23 - Nov 24 includes taxes & fees 8.6/10 Excellent! (1,014 reviews) [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) Still don't see what you're looking for? [See all properties in St. Michaels.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=5940&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=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=5940&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=5940&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=5940&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=5940&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=5940&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 St. Michaels Stroll down charming streets lined with boutiques and seafood restaurants in this quaint Chesapeake Bay town. Sail on a skipjack, visit the maritime museum, or bike to nearby wineries for a taste of Eastern Shore living. [See all hotels in St. Michaels](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&adults=2®ionId=5940) ![The Chesapeake Bay Maritime Museum in Saint Michaels, Maryland, features the Hooper Strait Lighthouse, built in 1879](https://images.trvl-media.com/place/5940/6d454cf3-0755-44c6-999f-dfbbe160658d.jpg?impolicy=fcrop&w=900&h=602&p=1&q=high) ## Top St. Michaels Hotel Reviews ![Inn at Perry Cabin](//images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg) ### Inn at Perry Cabin 10/10 Excellent "Friendly and attentive staff, good cleaning services" [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ## Find out more about St. Michaels ## Five Star Hotels in St. Michaels 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 St. Michaels 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 St. Michaels and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in St. Michaels 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 St. Michaels The results are in, and St. Michaels 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 St. Michaels! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in St. Michaels today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### What are the best 5-star hotels in St. Michaels? > Boasting premium amenities and guest services, our travellers rate [Inn at Perry Cabin](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) as one of the top 5-star hotels in St. Michaels. You'll be immersed in a world of luxury from the second you step into the lobby. ### How much does it cost to stay in a 5-star hotel in St. Michaels? > The amount you pay for a 5-star hotel in St. Michaels depends on factors such as when you want to go and the length of your stay. Our insider tip for scoring an awesome deal? Use our pricing filters to compare the available accommodations for your preferred dates. > > > > - Search for the lowest price per night from CA $156 ### What makes a hotel 5 stars in St. Michaels? > Outstanding guest service is integral to every 5-star hotel in St. Michaels. From the second you arrive, staff cater to your every whim, whether arranging customized tours or providing a nightly turn-down service. Additionally, hotels must offer top-rate conveniences to meet the standard for a 5-star rating. 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