Title: Book the Best Hotels with POOL in Eastern Shore in 2025 | Expedia.ca [Eastern Shore Travel Guide](https://expedia.ca/Eastern-Shore.dx6025644)[Hotels in Eastern Shore](https://expedia.ca/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels)[Vacation Rentals in Eastern Shore](https://expedia.ca/Eastern-Shore-Vacation-Rentals.d6025644.Travel-Guide-VacationRentals)[Flights to Eastern Shore](https://expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)[Things to do in Eastern Shore](https://expedia.ca/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities)[Eastern Shore Car Rentals](https://expedia.ca/Car-Rentals-In-Eastern-Shore.d6025644.Car-Rental-Guide)[Eastern Shore Vacation Packages](https://expedia.ca/Eastern-Shore.d6025644.Destination-Travel-Guides) ![Choptank River Lighthouse](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253262-Eastern-Maryland.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Eastern Shore, MD ![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 Eastern Shore Hotels with a Pool Tonight [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-04&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-05&endDate=2025-10-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastern Shore Hotels with a Pool ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/89000000/88280000/88274200/88274122/7dba1f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/89000000/88280000/88274200/88274122/69e18127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/89000000/88280000/88274200/88274122/07275524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/89000000/88280000/88274200/88274122/17474cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dunes Suites Oceanfront Midtown Ocean City 9.2/10 Wonderful (1087) "Beautiful view and nice accommodations. " CA $98 CA $109 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Suites-Oceanfront.h88274122.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2557x3y4-d297081d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily breakfast for a fee](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/72680920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2546x3y0-2a92d744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/8cb72b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Ocean City / Oceanfront Downtown Ocean City 9.0/10 Wonderful (1552) "The hotel and staff were great we will be back." CA $117 CA $130 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/580000/570300/570278/f06ec72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed, Non Smoking, City View | View from room](https://images.trvl-media.com/lodging/1000000/580000/570300/570278/a89967ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/580000/570300/570278/51e3d9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/580000/570300/570278/cf5451de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Ocean City Boardwalk Downtown Ocean City 9.0/10 Wonderful (1006) "Very nice rooms and accommodating staff" CA $102 CA $113 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Comfort-Inn-Boardwalk.h570278.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/f4ffab6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/4cb67a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/3a0853bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/b98ae621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Hotel Ocean City Oceanfront Downtown Ocean City 9.0/10 Wonderful (3226) "My family and I love that place" CA $97 CA $130 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879813/51dd071f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879813/135050f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879813/435b930e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879813/3b7ffdb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Ocean City Bayside Midtown Ocean City 9.0/10 Wonderful (1000) "Very beautiful and accommodating. Breakfast was awesome and had nice restaurants around" CA $100 CA $111 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Tru-By-Hilton-Ocean-City-Bayside.h48879813.Hotel-Information) ![Indoor pool, open 6:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/2ddc1565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/53741b4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach yoga](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/10d78993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/045cc807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Ocean City Oceanfront Midtown Ocean City 9.0/10 Wonderful (1027) "Loved our stay,the rooms are spacious and clean, very friendly hotel personal. Looking forward to our next stay. " CA $117 CA $130 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) ![Indoor pool, seasonal outdoor pool, lifeguards on site](https://images.trvl-media.com/lodging/2000000/1160000/1152000/1152000/dbae5ee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/2000000/1160000/1152000/1152000/c9025d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-golf](https://images.trvl-media.com/lodging/2000000/1160000/1152000/1152000/92c24b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, lifeguards on site](https://images.trvl-media.com/lodging/2000000/1160000/1152000/1152000/aafa401a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Francis Scott Key Family Resort West Ocean City 8.6/10 Excellent (15) "The front desk lady was a wonderful, helpful person. Sweet personality as well as knowledgeable. " CA $80 CA $116 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Ocean-City-Hotels-Francis-Scott-Key-Family-Resort.h1152000.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2300/2292/3a8b4ee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/10000/2300/2292/e439a1ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2300/2292/212b280e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/10000/2300/2292/65279325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront Downtown Ocean City 9.2/10 Wonderful (1094) "We stay here every summer and love it!" CA $107 CA $121 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Howard-Johnson-Plaza-Hotel-By-Wyndham-Ocean-City-Oceanfront.h2292.Hotel-Information) ![Indoor pool, outdoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9720000/9713100/9713072/d153273c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/10000000/9720000/9713100/9713072/d26aa0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/10000000/9720000/9713100/9713072/3068ea39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Balcony | Living area](https://images.trvl-media.com/lodging/10000000/9720000/9713100/9713072/1d0adef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Commander Hotel & Suites Downtown Ocean City 8.6/10 Excellent (1001) "Our favorite place to stay. " CA $89 CA $99 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Ocean-City-Hotels-Commander-Hotel-Suites.h9713072.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665366/5c59b6cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665366/cfaf0415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking (Efficiency)](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665366/22b15965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily breakfast](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665366/9ad837e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mainstay Suites Ocean City West West Ocean City 8.8/10 Excellent (224) "Staff & rooms were very clean & very roomy " CA $94 CA $104 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Ocean-City-Hotels-Mainstay-Suites-Ocean-City-West.h99665366.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=2025-10-18&endDate=2025-10-19®ionId=6025644&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Eastern Shore Hotel Reviews ![Carousel Resort Hotel & Condominiums](//images.trvl-media.com/lodging/1000000/20000/16200/16138/72fa8dcb_y.jpg) ### Carousel Resort Hotel & Condominiums 10/10 Excellent "How they had everything at your fingertips." [](https://expedia.ca/Ocean-City-Hotels-Carousel-Resort-Hotel-Condominiums.h16138.Hotel-Information) ![Ashore Resort & Beach Club](//images.trvl-media.com/lodging/1000000/30000/20400/20346/e36f7efc_y.jpg) ### Ashore Resort & Beach Club 10/10 Excellent "The hotel was uptown . It was quiet but I missed being by the boardwalk." [](https://expedia.ca/Ocean-City-Hotels-Clarion-Resort-Fontainebleau-Hotel-Oceanfront.h20346.Hotel-Information) ![Crystal Beach Hotel](//images.trvl-media.com/lodging/5000000/4590000/4584500/4584433/c45fe589_y.jpg) ### Crystal Beach Hotel 10/10 Excellent "Nice Hotel " [](https://expedia.ca/Ocean-City-Hotels-Crystal-Beach-Hotel.h4584433.Hotel-Information) ![Grand Hotel Ocean City Oceanfront](//images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg) ### Grand Hotel Ocean City Oceanfront 10/10 Excellent "Yes wonderful view " [](https://expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) ![Fenwick Inn](//images.trvl-media.com/lodging/1000000/70000/63000/62960/971dc050_y.jpg) ### Fenwick Inn 10/10 Excellent "Shops nearby" [](https://expedia.ca/Ocean-City-Hotels-Fenwick-Inn.h62960.Hotel-Information) ![Princess Royale Oceanfront Resort](//images.trvl-media.com/lodging/1000000/30000/22000/21981/b0fe2b94_y.jpg) ### Princess Royale Oceanfront Resort 10/10 Excellent "Great view " [](https://expedia.ca/Ocean-City-Hotels-Princess-Royale-Oceanfront-Resort.h21981.Hotel-Information) ![Quality Inn Ocean City Beachfront](//images.trvl-media.com/lodging/1000000/10000/6800/6796/e31fb3ed_y.jpg) ### Quality Inn Ocean City Beachfront 10/10 Excellent "Good times" [](https://expedia.ca/Ocean-City-Hotels-Econo-Lodge-Oceanfront.h6796.Hotel-Information) ![Hotel Monte Carlo Ocean City](//images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/8bf1c888_y.jpg) ### Hotel Monte Carlo Ocean City 10/10 Excellent "It was great !" [](https://expedia.ca/Ocean-City-Hotels-Hotel-Monte-Carlo-Ocean-City.h1866913.Hotel-Information) ![The Americana Hotel](//images.trvl-media.com/lodging/14000000/13280000/13279700/13279694/fc3af3e9_y.jpg) ### The Americana Hotel 10/10 Excellent "The hotel was very clean and newly renovated. The view was great and it was not a far walk to the music fest. We will definitely recommend and stay again. Thank you for making our trip a great one " [](https://expedia.ca/Ocean-City-Hotels-The-Americana-Hotel.h13279694.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [5 Star Hotels in St. Michaels](https://www.expedia.ca/5Star-St-Michaels-Hotels.s50-0-d5940.Travel-Guide-Filter-Hotels) - [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) - 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