Title: Book the Best St. Michaels LUXURY Hotels - Upscale Hotels in St. Michaels, MD | Expedia.ca [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) # Find luxury hotels in St. Michaels, MD - ![](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 Luxury Hotels Tonight [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-12-14&endDate=2025-12-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-12-15&endDate=2025-12-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for St. Michaels luxury 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) ![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) ![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/7a7c860e.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 (371) "Friendly and attentive staff, good cleaning services" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan CA $719 CA $870 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/e94a05fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/900/846/237feb4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/48975360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) Annapolis 9.4/10 Exceptional (1002) "Very nice hotel. The dog park could have better lighting. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $184 CA $210 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/c21b600a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/3952dad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis [](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) Annapolis 8.6/10 Excellent (1009) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tawnya CA $105 CA $120 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/add99640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/dac34e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/9e0f5859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chesapeake Bay [](https://www.expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) Cambridge 8.8/10 Excellent (1002) "Very courteous staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $208 CA $274 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/96f9cffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/0684bd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Annapolis [](https://www.expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) Annapolis 8.6/10 Excellent (1000) "Spectacular " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis CA $212 CA $242 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/462e7c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Single Room](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/ece40ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/49680cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) Stevensville 9.4/10 Exceptional (430) "Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DEANNA CA $253 CA $316 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/4dba2228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Balcony](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) Historic District 8.8/10 Excellent (882) "Great location, nice and clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Micah CA $245 CA $279 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/18678d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Cottage, 1 King Bed, River View](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/c5479a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d1a8f617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/6aa17d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oaks Waterfront [](https://www.expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) Easton 10/10 Exceptional (41) "Loved the Oaks! Fabulous accommodations and excellent staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $569 CA $626 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/d3121313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/230b1a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4750fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) Chesapeake Beach 8.4/10 Very good (1001) "The hotel is beautiful I can’t wait for" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $146 CA $190 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Dock](https://images.trvl-media.com/lodging/30000000/29320000/29313500/29313486/6c5e583a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/30000000/29320000/29313500/29313486/e6e9277d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/30000000/29320000/29313500/29313486/1fd64288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/30000000/29320000/29313500/29313486/7c99b5c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marvel's on the Creek [](https://www.expedia.ca/Secretary-Hotels-Marvels-On-The-Creek.h29313486.Hotel-Information) East New Market 10/10 Exceptional (161) "Clean & spacious room. Amazing hospitality. Excellent communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chin CA $256 CA $285 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Secretary-Hotels-Marvels-On-The-Creek.h29313486.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29®ionId=5940&adults=2&sort=LUXURY&star=50&openPlayBack=true) ## Top St. Michaels Hotel Reviews ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "Courteous and helpful staff. Very clean. " [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking." [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Clean upscale rooom..bed was amazing " [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet." [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "Spectacular " [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Excellent from check in to check out, highly recommend!" [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg) ### Hyatt Regency Chesapeake Bay 10/10 Excellent "Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience. " [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Very nice hotel. The dog park could have better lighting. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Room was good " [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ## Frequently asked questions ### Are you searching for the perfect hotel for your luxury trip to St. Michaels? ### What's the best luxury place to stay in St. Michaels? ### When can I expect good weather in St. Michaels? ### What's there to see and do in St. Michaels? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Hotels near Avalon Theatre ](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - 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