Title: Book the Best Hotels with POOL 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 Hotels with a Pool in St. Michaels, MD from CA $141 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Hotels with a Pool Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-07&endDate=2025-10-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top St. Michaels Hotels with a Pool ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/67743db3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Second Floor Bay View Double Room with Balcony ](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/4f8f8af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/e01c273a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/1e3401a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knapps Narrows Marina & Inn Tilghman 9.4/10 Exceptional (342) "Beautiful view!" CA $140 CA $153 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/97d2d16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG Grasonville 9.2/10 Wonderful (903) "The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!" CA $177 CA $197 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/72010305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/f2afc3df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Zen Cottage | Living area](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/7be1e889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/8889a53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Huntingfield Creek Rock Hall 10/10 Exceptional (53) "Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. " CA $195 CA $217 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/26f606ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/5f0e7ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/ac21726a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/76eda657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St Michaels Inn St. Michaels 8.2/10 Very good (1002) "Great location, free parking, free breakfast excellent staff." CA $128 CA $141 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/65faa113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/81d032fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Luxury Double, King Jacuzzi with fireplace](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/aeffd976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Deluxe Double, queen fire place](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/6d7108e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### George Brooks House B&B St. Michaels 8.6/10 Excellent (64) "Gorgeous quaint historic house. Friendly owner, close to town " CA $276 CA $304 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/8e209338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #2, King with Balcony](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/23402709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 2 Bedrooms, Balcony | Room amenity](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/23007304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/e07c03ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parsonage Inn St. Michaels 9.2/10 Wonderful (130) "Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!" CA $320 CA $351 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/760a2c92.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) ![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 (364) "Beautiful place to stay." CA $697 CA $843 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.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](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0efeb5e9.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 detail](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/72a927ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Tilghman Island Tilghman 8.8/10 Excellent (82) "Very relaxing stay." CA $236 CA $321 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Ballroom](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b42a3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (421) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " CA $272 CA $337 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/3f583294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/c423f238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/85e817af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/c4d91e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mariners Motel Rock Hall 9.4/10 Exceptional (90) "Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. " CA $201 CA $223 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Rock-Hall-Hotels-Mariners-Motel.h9330578.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=2025-10-20&endDate=2025-10-21®ionId=5940&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top St. Michaels Hotel Reviews ![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) ![Hyatt Regency Chesapeake Bay](//images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg) ### Hyatt Regency Chesapeake Bay 10/10 Excellent "Hyatt regency is more like a Hyatt place … fewer people working , in room dining is in paper boxes with plastic cutlery , but still regency pricing . But excellent pet policy and everyone so kind to pets " [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "The hotel was nice. The first room I got was still a mess because housekeeping didn’t clean that room. So I was given another room, which was clean as a whistle. Very good stay. I would definitely go back. Service was top tier." [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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 "Yes" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Great place." [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.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 "It was a very comfortable place, ver nice atmosphere." [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Easy Check In & quite area" [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Inn at Perry Cabin](//images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg) ### Inn at Perry Cabin 10/10 Excellent "Nice place to stay. Thru can’t do enough for you to make your stay comfortable and enjoyable Rooms are beautiful and clean " [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.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 "I truly enjoyed the location and convenience the easy access to highways " [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in St. Michaels? > [St Michaels Inn](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information): Features daily, a seasonal outdoor pool, and free self parking. [The Wildset](https://www.expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information): Provides a full-service spa, an outdoor pool, and 2 bars. [Inn at Perry Cabin](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information): Features free self parking, an outdoor pool, and complimentary wireless internet access. [George Brooks House B&B](https://www.expedia.ca/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information): Features kitchens, a communal pool, and televisions. [Parsonage Inn](https://www.expedia.ca/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information): Offers kitchens, a communal pool, and televisions. ### What is there to see and do in St. Michaels? > Make a point to visit attractions like Church Cove Park and Chesapeake Bay Maritime Museum. Discover sights such as St. Michaels Marina, St. Michaels Winery, and St. Michaels Museum during your stay. The seafood restaurants, historic landmarks, and shopping are just some of the things to enjoy while you're in the area. ### When is the best time to book a hotel with a pool in St. Michaels? > You may want to consider an accommodation with an outdoor swimming pool if you plan to visit St. Michaels in the warmest months of July, August, or June when the average temperature is 75°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 41°F. ## 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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