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) ![](https://images.trvl-media.com/place/177517/30c1fc19-3278-4d8b-9ab8-b49b3730e600.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 21 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-02-21&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 22 - Feb 23](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-02-22&endDate=2026-02-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake City hotels with a pool ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/120e15ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/628c8639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/96caeac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/75af64ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express North East by IHG [](https://www.expedia.ca/North-East-Hotels-Holiday-Inn-Express-North-East.h984873.Hotel-Information) North East 8.4/10 Very good (556 reviews) "The room was clean and the staff was friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Jane CA $122 CA $136 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/North-East-Hotels-Holiday-Inn-Express-North-East.h984873.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) ![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) ![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) ### 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 (349 reviews) "Awesome staff, very clean, great pool Awesome breakfast!!! All good things" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patty CA $134 CA $150 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) ![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 (347 reviews) "Clean room, great staff, recommended. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $135 CA $150 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/3633d98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/d850b13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a7c447e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) Aberdeen 9.0/10 Wonderful (1,007 reviews) "Everything was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) juan CA $113 CA $126 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.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) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/a5dd00be.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/3000000/2810000/2804400/2804384/1c5b9984.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 (639 reviews) "Quiet, clean, and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $127 CA $142 total includes taxes & fees Mar 6 - Mar 7 [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/418e7e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/2279c753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/cf0869c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/f058e662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Bel Air [](https://www.expedia.ca/Bel-Air-Hotels-Homewood-Suites-By-Hilton-Bel-Air.h2774553.Hotel-Information) Bel Air 8.8/10 Excellent (463 reviews) "Yes we enjoyed it all staff was great felt like they really cared" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex CA $128 CA $143 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Bel-Air-Hotels-Homewood-Suites-By-Hilton-Bel-Air.h2774553.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) ![Premium bedding, pillowtop beds, in-room safe, individually furnished](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/22921f08.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) ### 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 (804 reviews) "Very clean, staff was very cordial and the breakfast buffet is great. Definitely recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $156 CA $173 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Wilmington-Hotels-SpringHill-Suites-By-Marriott-Newark-Downtown.h23089234.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/00ecda1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/ce28b46d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/b0fa8511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Aberdeen near APG [](https://www.expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) Aberdeen 8.0/10 Very good (850 reviews) "Room was nice area was good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Armond CA $98 CA $109 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/60000/50200/50134/0adbdd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/60000/50200/50134/53e9ad31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/60000/50200/50134/0d7cdfaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50134/640b7870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites North East [](https://www.expedia.ca/North-East-Hotels-Comfort-Inn-And-Suites.h50134.Hotel-Information) North East 7.8/10 Good (661 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina CA $113 CA $126 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/North-East-Hotels-Comfort-Inn-And-Suites.h50134.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/5ae9ccb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/48cb4ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/fa561265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/1c3a6583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD [](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information) Bel Air 8.8/10 Excellent (1,001 reviews) "We always enjoy our stay here when visiting our family as the facility is clean, comfortable and quiet. Only exception was on one of the days a fire alarm had gone off and scared us awake but it turned out to be a false alarm. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryle CA $108 CA $121 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.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=2026-03-07&endDate=2026-03-08®ionId=177517&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Chesapeake City Breakfast included Hot tub 4 stars Ocean view 5 stars ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_177517) ## Top Chesapeake City Hotel Reviews ![Quality Inn Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg) ### Quality Inn Newark - Wilmington 10/10 Excellent "Nice people" [](https://expedia.ca/Wilmington-Hotels-Quality-Inn.h25008.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 "," [](https://expedia.ca/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information) ![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 "Breakfast was great quality." [](https://expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-Hotel-Suites-Wilmington-Newark.h14182.Hotel-Information) ![Hilton Wilmington/Christiana](https://images.trvl-media.com/lodging/1000000/10000/7100/7053/7640fa86_y.jpg) ### Hilton Wilmington/Christiana 10/10 Excellent "Greeted immediately for a kind very speedy check-in rooms were clean. Breakfast was delicious." [](https://expedia.ca/Wilmington-Hotels-Hilton-WilmingtonChristiana.h7053.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 very spacious love the amenities " [](https://expedia.ca/Wilmington-Hotels-Sonesta-ES-Suites-Wilmington-Newark.h19062.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 "Amenities and cleanliness" [](https://expedia.ca/Wilmington-Hotels-Embassy-Suites-Newark-WilmingtonSouth.h327586.Hotel-Information) ![Red Roof Inn PLUS+ Wilmington - Newark](https://images.trvl-media.com/lodging/1000000/10000/7900/7845/aa58fe8d_y.jpg) ### Red Roof Inn PLUS+ Wilmington - Newark 10/10 Excellent "Room was very clean" [](https://expedia.ca/Wilmington-Hotels-Red-Roof-Inn-PLUS-Wilmington-Newark.h7845.Hotel-Information) ![Ramada by Wyndham Newark/Wilmington](https://images.trvl-media.com/lodging/1000000/10000/9400/9312/f1191985_y.jpg) ### Ramada by Wyndham Newark/Wilmington 10/10 Excellent "Staff was very nice. They work with you with any need you have. Very helpful, rooms not as up to date as expected but the staff was good." [](https://expedia.ca/Wilmington-Hotels-Ramada-By-Wyndham-NewarkWilmington.h9312.Hotel-Information) ![Red Roof Inn & Suites Wilmington - New Castle](https://images.trvl-media.com/lodging/1000000/30000/25100/25051/3560c2da_y.jpg) ### Red Roof Inn & Suites Wilmington - New Castle 10/10 Excellent "The staff was very courteous. The room was nice and quiet. " [](https://expedia.ca/Wilmington-Hotels-Red-Roof-Inn-Suites-Wilmington-New-Castle.h25051.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 - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Cheap Hotels in Aberdeen ](https://www.expedia.ca/Aberdeen-Hotels-Cheap-Hotels.0-0-d6044-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Aberdeen ](https://www.expedia.ca/Aberdeen-Hotels-Family-Hotel.0-0-d6044-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Aberdeen ](https://www.expedia.ca/Aberdeen-Hotels-Hotels-With-Hot-Tubs.0-0-d6044-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Aberdeen ](https://www.expedia.ca/Aberdeen-Hotels-Pet-Friendly-Hotel.0-0-d6044-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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