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 $115 - ![](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 Oyster Harbor Hotels with a Pool Tonight [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&startDate=2025-11-05&endDate=2025-11-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&startDate=2025-11-06&endDate=2025-11-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&startDate=2025-11-14&endDate=2025-11-16&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) ![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) ![Balcony view](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/1e3401a3.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 (348) "Beautiful view!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chantel CA $141 CA $155 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.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) ![Marina](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/27bb8cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5.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 Chesapeake Beach 8.4/10 Very good (1000) "Our stay was great! No complaints at all." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane CA $127 CA $170 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.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/1000000/120000/117000/116919/5139c564.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) ### Holiday Inn Express Annapolis East-Kent Island by IHG Grasonville 9.2/10 Wonderful (914) "Excellent, pet friendly, clean, convenient, and beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $134 CA $149 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.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) ![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) ![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) ### St Michaels Inn St. Michaels 8.2/10 Very good (1000) "Great location, free parking, free breakfast excellent staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany CA $137 CA $151 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/6281ec00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/f7bcd5fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/9ddea0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/57bd9cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Annapolis Annapolis 8.2/10 Very good (1000) "I had a lovely stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kalynn CA $101 CA $115 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e7e5362c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/6846c015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/fbea7cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Annapolis Edgewater 8.8/10 Excellent (936) "Clean room and pleasant front desk staff. It’s a favorite place to stay whenever in the area! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brittany CA $119 CA $136 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/cfbb67fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/e2360421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/76f6e3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Annapolis by IHG Annapolis 8.8/10 Excellent (1020) "Nice and quiet, good and clean bed, big parking lot, exellent personel, not complains." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) martin CA $136 CA $155 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/19214323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/9e6dd0ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Annapolis, MD Annapolis 9.0/10 Wonderful (1000) "Staff was very friendly answering all questions, room was clean and very comfortable bed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frances CA $136 CA $155 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/068178f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/cc651796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/160d338a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn Grasonville 8.0/10 Very good (1000) "The experience was as expected. Everything worked well and the staff were very friendly. I would recommend this hotel for a short stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bernadette CA $129 CA $144 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9744c10d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/bdf87bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina Grasonville 9.4/10 Exceptional (648) "My favorite hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jen CA $190 CA $211 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.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=2025-11-19&endDate=2025-11-20®ionId=553248635976482330&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Oyster Harbor 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 "The staff was friendly and the room was nice and clean. Very happy!! Tom" [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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 "Staff was very friendly answering all questions, room was clean and very comfortable bed" [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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 "The breakfast was great including domethong for everyone. You can make your own waffles as well as enjoy eggs, breakfast meat toast, bagels and fruit." [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Best hotel in its price range." [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.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 "Room was comfortable and the staff were courtesy!" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 "Nice room and lovelt spacial areas" [](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.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 "Awesome " [](https://expedia.ca/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.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 "I am a healthcare traveler and I work night shift. Unlike most people who go to a hotel, i need a bed for day time sleep and an esrly check in. The front desk agents accommodated my early check in and gave me a clean room at 9am. I went to sleep right away. No noise, no dirty bathroom. Plus the buffet was a huge plus. I booked all my other stays here. This will be home for the next couple of weeks. Everyone had a welcoming smile. " [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Hampton Inn Bowie](//images.trvl-media.com/lodging/1000000/430000/424900/424888/0eac7056_y.jpg) ### Hampton Inn Bowie 10/10 Excellent "Every staff was friendly and professional from the door to the EVS ladies helping to clean or supply towels. I enjoyed my stay and slept good as well.😊" [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Bowie.h424888.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): Provides buffet, an indoor pool, and free self parking. [Graduate by Hilton Annapolis](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information): Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. [Country Inn & Suites by Radisson, Annapolis, MD](https://www.expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information): Offers buffet, a seasonal outdoor pool, and free self parking. [Sonesta ES Suites Annapolis](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information): Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. [Comfort Inn Conference Center](https://www.expedia.ca/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information): Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool, and a snack bar/deli. ### What is there to see and do in Oyster Harbor? > Spend some time experiencing the great outdoors at Chesapeake Bay. Discover sights such as Northern Chesapeake Bay 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. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temperature is 40°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [4 Star Hotels in Anchorage](https://www.expedia.ca/4Star-Anchorage-Annapolis-Hotels.s40-n553248635976473602-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Annapolis](https://www.expedia.ca/4Star-Annapolis-Hotels.s40-0-d6034082.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Adults-Only-Resorts.0-n553248635976473602-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Boutique-Hotel.0-n553248635976473602-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Historic-Hotel.0-n553248635976473602-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - 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