Title: 5 Stars Hotels in St. Michaels, Maryland from CA $140 - 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) ![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=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/5940/6d454cf3-0755-44c6-999f-dfbbe160658d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Mar 25 - Mar 26](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2026-03-25&endDate=2026-03-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 26 - Mar 27](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2026-03-26&endDate=2026-03-27&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2026-03-27&endDate=2026-03-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2026-04-03&endDate=2026-04-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for St. Michaels 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) ![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) ![Staircase](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/4ea15d12.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.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) Downtown St. Michaels 9.6/10 Exceptional (374 reviews) "Fantastic - loved our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily CA $550 CA $605 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/6a67d68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/5726b171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/b1c929dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/d7ca8491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate [](https://www.expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) Tracys Landing 9.4/10 Exceptional (12 reviews) "Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend \*\*\*\*\*" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd [](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) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/3f44a760.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) ![Interior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/20605cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at 202 Dover [](https://www.expedia.ca/Easton-Hotels-Inn-At-202-Dover.h5308723.Hotel-Information) Easton 10/10 Exceptional (14 reviews) "Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James [](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/ca081b22_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Graduate by Hilton Annapolis 126 West St Annapolis MD CA $245 CA $279 total Apr 19 - Apr 20 includes taxes & fees 9.4/10 Exceptional! (1,001 reviews) [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Annapolis Waterfront Hotel, Autograph Collection 80 Compromise St Annapolis MD CA $290 CA $331 total Apr 12 - Apr 13 includes taxes & fees 8.8/10 Excellent! (912 reviews) [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Annapolis 210 Holiday Court Annapolis MD CA $123 CA $140 total Mar 29 - Mar 30 includes taxes & fees 8.6/10 Excellent! (1,010 reviews) [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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=26%2F03%2F2026&endDate=27%2F03%2F2026®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=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=5940&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=5940&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=5940&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=5940&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®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=2026-04-08&endDate=2026-04-09&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](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd_y.jpg) ### Inn at Perry Cabin 10/10 Excellent "We had a great stay, hotel was very clean and food was great" [](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? ### How much does it cost to stay in a 5-star hotel in St. Michaels? > - Search for the lowest price per night from CA $140 ### What makes a hotel 5 stars in St. Michaels? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [1 Star Hotels in Holabird Industrial Park ](https://www.expedia.ca/1Star-Holabird-Industrial-Park-Baltimore-Hotels.s10-n553248635976387003-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Cheltenham ](https://www.expedia.ca/2Star-Cheltenham-Hotels.s20-0-d553248635975874284.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Graceland Park ](https://www.expedia.ca/3Star-Graceland-Park-Baltimore-Hotels.s30-n553248635976385043-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Algonquin ](https://www.expedia.ca/4Star-Algonquin-Hotels.s40-0-d553248635975860123.Travel-Guide-Filter-Hotels) - 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