Title: Book the Best Hotels with POOL in Winchester-on-the-Severn in 2026 | 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)[Winchester-on-the-Severn Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester-On-The-Severn.d553248635976475477.Car-Rental-Guide)[Winchester-on-the-Severn Vacations](https://expedia.ca/Winchester-On-The-Severn.d553248635976475477.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winchester-on-the-Severn, MD from CA $117 - ![](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 Winchester-on-the-Severn Hotels with a Pool Tonight [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-12-16&endDate=2025-12-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-12-17&endDate=2025-12-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester-on-the-Severn hotels with a pool ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.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/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (934) "It was very comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $120 CA $133 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.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/w5759h3834x0y6-7304a3c1.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 [](https://www.expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) Annapolis 8.8/10 Excellent (1005) "Excellent from check in to check out, highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $151 CA $173 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/3b4c6941.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) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/88c6362a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/a8a9cf9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (674) "Great view, good ambiance all around" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dianne CA $151 CA $168 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Indoor pool, open 5 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/b307a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/d03cf3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/e17d8d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) Grasonville 9.0/10 Wonderful (1002) "Room was clean The staff was excellent.we were greeted each morning with a smile when we came down for coffee. Great service from Sarah in the evening " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teresa CA $146 CA $162 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.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) ![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) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn [](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) Grasonville 8.0/10 Very good (1004) "Our room was clean, smelled great, and the breakfast was good with many options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $115 CA $127 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/6281ec00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/7f54b5f9.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) ![Hypo-allergenic bedding, down comforters, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/f7bcd5fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information) Annapolis 8.2/10 Very good (1001) "Clean room, fast and easy check in, made to order breakfast options. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $102 CA $117 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7f9539e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/abc30633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7e58a966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) Annapolis 8.6/10 Excellent (1002) "Wonderful stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela CA $116 CA $132 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/662e8b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Balcony](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/85bd6071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8dfe0c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/814e7667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anchored Inn at Hidden Harbour Marina [](https://www.expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) Deale 9.4/10 Exceptional (470) CA $185 CA $211 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.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 near Kent Island [](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) Grasonville 7.8/10 Good (863) "room was nice breakfast was good and the staff was very friendly and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Esai CA $117 CA $130 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (128) "The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $197 CA $268 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.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=2025-12-30&endDate=2025-12-31®ionId=553248635976475477&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester-on-the-Severn Hotel Reviews ![La Quinta Inn & Suites by Wyndham Baltimore BWI Airport](https://images.trvl-media.com/lodging/1000000/30000/25900/25898/941fbe1a_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore BWI Airport 10/10 Excellent "Clean room and staff were " [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-BWI-Airport.h25898.Hotel-Information) ![Aloft BWI Baltimore Washington International Airport](https://images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/12d1a93d_y.jpg) ### Aloft BWI Baltimore Washington International Airport 10/10 Excellent "Everything " [](https://expedia.ca/Baltimore-Hotels-Aloft-BWI-Baltimore-Washington-International-Airport.h2804098.Hotel-Information) ![Sonesta ES Suites Baltimore BWI Airport](https://images.trvl-media.com/lodging/1000000/80000/77900/77835/1f717877_y.jpg) ### Sonesta ES Suites Baltimore BWI Airport 10/10 Excellent "I came for the Army/Navy game. Had a great experience overall. The staff was very friendly; room was clean; breakfast was nice and healthy. Highly recommend " [](https://expedia.ca/Baltimore-Hotels-Sonesta-ES-Suites-Baltimore-BWI-Airport.h77835.Hotel-Information) ![Wingate by Wyndham Baltimore BWI Airport](https://images.trvl-media.com/lodging/1000000/20000/12700/12658/576f84db_y.jpg) ### Wingate by Wyndham Baltimore BWI Airport 10/10 Excellent "We had such a great time. I was disappointed when I read some reviews. But soo happy I did not listen to them. The staff was excellent location to stadium perfect. Shuttle was above and beyond. We all 6 of us 4 rooms 2 nights have no complaints and will stay again " [](https://expedia.ca/Baltimore-Hotels-Wingate-By-Wyndham-Baltimore-BWI-Airport.h12658.Hotel-Information) ![Holiday Inn Columbia East-Jessup by IHG](https://images.trvl-media.com/lodging/1000000/20000/15800/15724/6a8978a8_y.jpg) ### Holiday Inn Columbia East-Jessup by IHG 10/10 Excellent "Jessica at the front desk was so kind and helpful. The room was clean. " [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Columbia-East-Jessup.h15724.Hotel-Information) ![Motel 6 Laurel, DC - Washington Northeast](https://images.trvl-media.com/lodging/2000000/1040000/1037800/1037774/e7095d28_y.jpg) ### Motel 6 Laurel, DC - Washington Northeast 10/10 Excellent "Staff" [](https://expedia.ca/Baltimore-Hotels-Motel-6-Laurel.h1037774.Hotel-Information) ![Hilton Baltimore BWI Airport](https://images.trvl-media.com/lodging/2000000/1520000/1518600/1518537/78c7fba5_y.jpg) ### Hilton Baltimore BWI Airport 10/10 Excellent "Nice hotel " [](https://expedia.ca/Baltimore-Hotels-Hilton-Baltimore-BWI-Airport.h1518537.Hotel-Information) ![SpringHill Suites by Marriott Baltimore BWI Airport](https://images.trvl-media.com/lodging/1000000/580000/574400/574327/c40dfb4d_y.jpg) ### SpringHill Suites by Marriott Baltimore BWI Airport 10/10 Excellent "It checked all the boxes of what i need. Thanks!" [](https://expedia.ca/Baltimore-Hotels-SpringHill-Suites-By-Marriott-Baltimore-BWI-Airport.h574327.Hotel-Information) ![The Hotel at Arundel Preserve](https://images.trvl-media.com/lodging/5000000/4550000/4542400/4542302/bd8bd966_y.jpg) ### The Hotel at Arundel Preserve 10/10 Excellent "Great" [](https://expedia.ca/Baltimore-Hotels-The-Hotel-At-Arundel-Preserve.h4542302.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winchester-on-the-Severn? ### What is there to see and do in Winchester-on-the-Severn? ### When is the best time to book a hotel with a pool in Winchester-on-the-Severn? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Epping Forest ](https://www.expedia.ca/5Star-Epping-Forest-Annapolis-Hotels.s50-n553248635976473158-0.Travel-Guide-Filter-Hotels) - [Annapolis Hotels ](https://www.expedia.ca/Annapolis-Hotels.d6034082.Travel-Guide-Hotels) - 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