Title: Book the Best Hotels with POOL in Chesapeake City in 2026 | Expedia.ca [Chesapeake City Travel Guide](https://expedia.ca/Chesapeake-City.dx177517)[Hotels in Chesapeake City](https://expedia.ca/Chesapeake-City-Hotels.d177517.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake City](https://expedia.ca/Chesapeake-City-Vacation-Rentals.d177517.Travel-Guide-VacationRentals)[Chesapeake City Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake-City.d177517.Car-Rental-Guide)[Chesapeake City Vacation Packages](https://expedia.ca/Chesapeake-City.d177517.Destination-Travel-Guides) ![An aerial view of historic Annapolis, situated on the Chesapeake Bay, during an early November morning.](https://images.trvl-media.com/place/177517/30c1fc19-3278-4d8b-9ab8-b49b3730e600.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Chesapeake City, MD from CA $104 - ![](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 Chesapeake City Hotels with a Pool Tonight [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2025-12-21&endDate=2025-12-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2025-12-22&endDate=2025-12-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake City hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/791afcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/fd2dd5eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/a0c80d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Middletown [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) Middletown 9.2/10 Wonderful (322) "The room was spotless, courteous staff, and a wonderful breakfast to start my day " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan CA $149 CA $165 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/0e7e3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/12e386c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/1d870257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/587ee69d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Newark, DE [](https://www.expedia.ca/Newark-Hotels-Residence-Inn-By-Marriott-Newark.h116852262.Hotel-Information) Newark 8.8/10 Excellent (15) "Nice room, clean, big, and well appointed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $139 CA $155 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Newark-Hotels-Residence-Inn-By-Marriott-Newark.h116852262.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/f97697a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/6d4bf88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/18ef6405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/76694a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Wilmington-Newark by IHG [](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-Hotel-Suites-Wilmington-Newark.h14182.Hotel-Information) Newark 9.4/10 Exceptional (1003) "Everything was just right. Great breakfast Friendly, helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $135 CA $150 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-Hotel-Suites-Wilmington-Newark.h14182.Hotel-Information) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/b90292fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/8628f41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/735621f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/817be2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Smyrna [](https://www.expedia.ca/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information) Smyrna 7.6/10 Good (1002) "Very pleasant experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $94 CA $104 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/a4f6753f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/a3a44793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/1f832bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave (with Sofabed)](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/2ca9a3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Newark/Christiana Inn [](https://www.expedia.ca/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information) Bear 8.4/10 Very good (89) "Clean room and convenient to highway." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $99 CA $109 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/7074520f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Accessible (Hearing)](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/w3837h2561x3y0-b0885367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/w3837h2547x3y4-94e4330e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/f0086565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Baltimore / Aberdeen, MD [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) Aberdeen 8.8/10 Excellent (338) "The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory CA $98 CA $110 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/b66763a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6a6a4995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/7e87d5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6cc4a825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Middletown [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) Middletown 8.8/10 Excellent (863) "The breakfast was was very good with lots of options depending on your dietary needs." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $131 CA $146 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/6039d933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/6ad2d4bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/015ae050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/79ddc1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Newark Downtown [](https://www.expedia.ca/Wilmington-Hotels-SpringHill-Suites-By-Marriott-Newark-Downtown.h23089234.Hotel-Information) Newark 9.4/10 Exceptional (762) "Clean room, good breakfast, nice staff. Easy experience for a great price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leigh CA $123 CA $136 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Wilmington-Hotels-SpringHill-Suites-By-Marriott-Newark-Downtown.h23089234.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/e4d0d0d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/c9c370cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/8a6e6273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/36d1df4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Newark - Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information) Newark 9.0/10 Wonderful (1060) "Excellent room, great, friendly staff and a great breakfast in the morning." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $116 CA $129 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/18e3859d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/3c250b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/fafda427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/a5dd00be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Aberdeen [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) Aberdeen 8.6/10 Excellent (633) "Close to restaurants, friendly staff, nice room, food was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peggy CA $121 CA $135 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.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=2026-01-04&endDate=2026-01-05®ionId=177517&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake City Hotel Reviews ![Holiday Inn Express & Suites Wilmington-Newark by IHG ](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/0462a60c_y.jpg) ### Holiday Inn Express & Suites Wilmington-Newark by IHG 10/10 Excellent "Everything was just right. Great breakfast Friendly, helpful staff" [](https://expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-Hotel-Suites-Wilmington-Newark.h14182.Hotel-Information) ![Embassy Suites by Hilton Newark Wilmington South](https://images.trvl-media.com/lodging/1000000/330000/327600/327586/b7951f6a_y.jpg) ### Embassy Suites by Hilton Newark Wilmington South 10/10 Excellent "Breakfast" [](https://expedia.ca/Wilmington-Hotels-Embassy-Suites-Newark-WilmingtonSouth.h327586.Hotel-Information) ![Homewood Suites by Hilton Newark-Wilmington South Area](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052325/2d7e7964_y.jpg) ### Homewood Suites by Hilton Newark-Wilmington South Area 10/10 Excellent "The staff was great....the room was OK....a bit dated but clean and had everything that was needed. I would stay again." [](https://expedia.ca/Wilmington-Hotels-Homewood-Suites-By-Hilton-Newark-Wilmington-South.h1052325.Hotel-Information) ![Sonesta Select Newark Christiana Mall](https://images.trvl-media.com/lodging/1000000/10000/2100/2091/5b01ae08_y.jpg) ### Sonesta Select Newark Christiana Mall 10/10 Excellent "The staff was fantastic very helpful, rooms was very nice and clean. " [](https://expedia.ca/Wilmington-Hotels-Sonesta-Select-Newark.h2091.Hotel-Information) ![Comfort Inn & Suites Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/ea219a4a_y.jpg) ### Comfort Inn & Suites Newark - Wilmington 10/10 Excellent "Very Clean , convenient location, very good breakfast buffet " [](https://expedia.ca/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information) ![Best Western Plus Newark/Christiana Inn](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/bb536b3a_y.jpg) ### Best Western Plus Newark/Christiana Inn 10/10 Excellent "Very clean and a friendly staff." [](https://expedia.ca/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information) ![Hilton Wilmington/Christiana](https://images.trvl-media.com/lodging/1000000/10000/7100/7053/7640fa86_y.jpg) ### Hilton Wilmington/Christiana 10/10 Excellent "The room could use some updating, but it was clean and comfortable." [](https://expedia.ca/Wilmington-Hotels-Hilton-WilmingtonChristiana.h7053.Hotel-Information) ![Quality Inn Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg) ### Quality Inn Newark - Wilmington 10/10 Excellent "Friendly staff clean room that was already warmed up when I walked through the door " [](https://expedia.ca/Wilmington-Hotels-Quality-Inn.h25008.Hotel-Information) ![Sonesta ES Suites Wilmington - Newark](https://images.trvl-media.com/lodging/1000000/20000/19100/19062/98de1f1c_y.jpg) ### Sonesta ES Suites Wilmington - Newark 10/10 Excellent "The room was clean, friendly staff, breakfast was great contained a variety of stuff " [](https://expedia.ca/Wilmington-Hotels-Sonesta-ES-Suites-Wilmington-Newark.h19062.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Chesapeake City? ### What is there to see and do in Chesapeake City? ### When is the best time to book a hotel with a pool in Chesapeake City? ## Explore a world of travel with Expedia - 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