Title: Book the Best HISTORIC Hotels in St. Michaels in 2025 | 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) ![](https://mediaim.expedia.com/destination/1/e708a2ddef7b36b18845a12b959447e3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in St. Michaels, MD from CA $214 ![](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 Historic Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top St. Michaels Historic Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/fc311cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/18961763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 1 King Bed (Safari Suite (at Tidewater House))](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/17d21ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/e0eae32d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tidewater Inn Easton 8.8/10 Excellent (832) "Great hotel! Stayed there multiple times." CA $251 CA $276 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/937d59ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/72a927ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Suite | Living area](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0787536d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0efeb5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Tilghman Island Tilghman 8.8/10 Excellent (83) "Very relaxing stay." CA $237 CA $323 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1847) "The hotel was absolutely clean and close to the shops and restaurants. " CA $145 CA $214 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/cc957ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/6c83d519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/fda5370c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/w1857h2500x0y0-ac5cefb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn Historic District 9.4/10 Exceptional (79) "Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!" CA $329 CA $375 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/a8bf1b01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/97119172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/8d2066be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/6d339134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 86 State Circle - Luxury Boutique Hotel Historic District 10/10 Exceptional (2) "Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels." CA $515 CA $588 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/1976e6ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/2624f48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Single Room, 1 King Bed, Bathtub, Harbour View](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/15680a18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/03fed2cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 134 Prince - Luxury Boutique Hotel Annapolis 9.8/10 Exceptional (26) "Very friendly staff!" CA $287 CA $328 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/5acb80c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis Historic District 10/10 Exceptional (71) "The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay" CA $183 CA $458 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/aaa820d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d4e67bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/520df554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/67700a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants North Beach 10/10 Exceptional (30) "Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. " CA $250 CA $701 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/1aa587de_edited_b1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h908x3y2-e4e5546a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h906x3y0-7a94439d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h906x3y0-2211d6c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Row Home 1 Block from Gate 1 at USNA! Historic District 10/10 Exceptional (2) "Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! " CA $217 CA $1,030 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-1-Block-From-Gate-1-At-USNA.h117588789.Hotel-Information) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/1b8e0fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/3c0a3b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/ed81b1a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/c86eb9a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★ Midcentury Modern Getaway ★ Prime Location ★ Historic District 10/10 Exceptional (35) "This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. " CA $273 CA $813 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Midcentury-Modern-Getaway-Prime-Location.h48624274.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=2025-10-27&endDate=2025-10-28®ionId=5940&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top St. Michaels Hotel Reviews ![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Our night at your hotel was just fine! Room was clean. Supply toiletries, towels for the bath and kitchen were as expected, neat and plentiful. There was a creak in the bathroom door, but that is a nitpick. Coffee maker was easy to operate. Breakfast was as expected, with some delay when coffee carafe and food service trays were empty. I would go back." [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "yes" [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](//images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "Bed linens were very disappointing. Pillows, sheets and blanket were flimsy and cheap. " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![SpringHill Suites by Marriott Annapolis](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 10/10 Excellent " Very clean and fresh room The TV screen already had my name on it !" [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "The staff were uniformly attentive and friendly." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Spacious room, very clean and comfortable lots of eclectic nautical furniture. We did not have breakfast. Easy parking in and out right in the heart of restaurants, & bars and a short walk to the harbor." [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Excellent stay but I never received my wine " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "very friendly personel" [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Great room." [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to St. Michaels? > Significant historical sites in St. Michaels are likely at the top of your travel itinerary. Visit the waterfront and shops while you're in town. During your stay in this romantic area, you can also relish a trip to the seafood restaurants. ### How many historically relevant hotels are there in St. Michaels? > St. Michaels is home to 66 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from. ### What are the most important historical places and other sights in St. Michaels? > St. Michaels is notable for landmarks like St. Michaels Museum. The picturesque setting of Church Cove Park and CL Open Field exemplify the area's natural beauty. A couple of additional sights to add to your agenda are St. Michaels Marina and Chesapeake Bay Maritime Museum. ### What is a historic hotel like in St. Michaels? > When you choose a historic hotel, you'll enjoy a vacation someplace that has an officially recognized national historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be transformed into a historic hotel provided that it has special significance. Traditional architecture and period features can be admired in the communal spaces and guestrooms of these historic hotels in St. Michaels, bringing the history to life. ### What is the difference between a historic hotel and a heritage hotel? > They are quite similar. The term "historic hotel" is more common in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to place more significance on the architecture and actual building. Heritage hotels draw their meaning mainly from the cultural value that the place has and how it inspired the community. ### Do historic hotels in St. Michaels have modern facilities? > Yes. Every effort is made to preserve historic facades and treasured traditions, but interiors include modern conveniences and safety features. Guests can expect the usual amenities you'd find in a hotel such as private rooms with updated bathroom facilities, WiFi, and more. In St. Michaels, booking a historic hotel doesn't mean you're picking a place that's uncomfortable for guests or simply rundown. ## 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) - [Apartments in Bellevue](https://www.expedia.ca/Bellevue-Apartments.d553248635975867527-aaApartments.Travel-Guide-Accommodation) - [Condo Rentals in Bellevue](https://www.expedia.ca/Bellevue-Condos.d553248635975867527-aaCondos.Travel-Guide-Accommodation) - [Motels in Bellevue](https://www.expedia.ca/Bellevue-Motels.d553248635975867527-aaMotels.Travel-Guide-Accommodation) - 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