Title: Book the Best Hotels with POOL in Oyster Harbor in 2025 | Expedia.ca [Vacation Rentals in Annapolis](https://expedia.ca/Annapolis-Vacation-Rentals.d6034082.Travel-Guide-VacationRentals)[Flights to Annapolis](https://expedia.ca/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)[Things to do in Annapolis](https://expedia.ca/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)[Oyster Harbor Car Rentals](https://expedia.ca/Car-Rentals-In-Oyster-Harbor.d553248635976482330.Car-Rental-Guide)[Oyster Harbor Vacations](https://expedia.ca/Oyster-Harbor.d553248635976482330.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/1c03078f1f729b58cd71995ee5e48d7d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by KaiG # Find Hotels with a Pool in Oyster Harbor, 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 Oyster Harbor Hotels with a Pool Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&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=553248635976482330&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=553248635976482330&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=553248635976482330&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oyster Harbor 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) ![Front of property](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/25d29217.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) ### 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 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/1000000/20000/10300/10281/08593556.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/5f0e7ddb.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) ![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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.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) ![Garden Cottage](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/5c79eae4.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) ![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](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/43940c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/925f7921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/d09846f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/5fd615f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Conference Center Bowie 9.2/10 Wonderful (1002) "Nice stay" CA $138 CA $156 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ![Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/9f6ae80a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite | Balcony](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5.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) ![Marina](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/27bb8cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort Chesapeake Beach 8.4/10 Very good (1001) "Great place to stay." CA $187 CA $236 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/ead5e21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/48d9bd9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Grasonville 7.8/10 Good (834) "Great place and great staff" CA $136 CA $151 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.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) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/72a927ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Widows Walk Suite | Terrace/patio](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/ba45b764.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) ![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 amenity](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/85e817af.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) ![Marina](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/149f435b.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=553248635976482330&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Oyster Harbor 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) ![Hilton Garden Inn Annapolis](//images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/f7bcd5fc_y.jpg) ### Hilton Garden Inn Annapolis 10/10 Excellent "Well appointed, clean, and wonderful beds!" [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.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) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "This hotel was fantastic. I’m not sure what I was expecting, but it exceeded any expectations I may have had. I would definitely stay here again!" [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Comfort Inn Conference Center](//images.trvl-media.com/lodging/1000000/20000/17300/17201/925f7921_y.jpg) ### Comfort Inn Conference Center 10/10 Excellent "Staff was super friendly and helpful. " [](https://expedia.ca/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ![Hampton Inn & Suites Annapolis](//images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg) ### Hampton Inn & Suites Annapolis 10/10 Excellent "Nice location and staff was friendly and helpful." [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![Courtyard by Marriott Annapolis](//images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3_y.jpg) ### Courtyard by Marriott Annapolis 10/10 Excellent "Extremely cozy. Felt good to just relax." [](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Oyster Harbor? > [Historic Inns of Annapolis](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information): Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. [Sonesta ES Suites Annapolis](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information): Provides buffet, an indoor pool, and free self parking. [Country Inn & Suites by Radisson, Annapolis, MD](https://www.expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information): Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. [Crowne Plaza Annapolis by IHG](https://www.expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information): Features buffet, a seasonal outdoor pool, and free self parking. [DoubleTree by Hilton Hotel Annapolis](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information): Provides daily, a pool, and free self parking. ### What is there to see and do in Oyster Harbor? > The picturesque setting of Bay Ridge Beach and Maryland Quiet Waters Park showcase the area's natural beauty. Discover sights such as Annapolis Landing Marina, Annapolis Maritime Museum, and Ego Alley during your stay. ### When is the best time to book a hotel with a pool in Oyster Harbor? > You may want to consider a place to stay that offers an outdoor if you're planning to visit in the warmest months of July, August, or June when the average temperature is 75°F. 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