Title: 4 Stars Hotels in Winchester-on-the-Severn, Annapolis from CA $156 - Find Cheap Winchester-on-the-Severn Hotels With 4 Stars | Expedia.ca [Winchester-on-the-Severn Travel Guide](https://expedia.ca/Annapolis-Winchester-On-The-Severn.dx553248635976475477)[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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Winchester-on-the-Severn, Annapolis from CA $156 ![](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 4 Star Hotels Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-10-19&endDate=2025-10-20&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-10-20&endDate=2025-10-21&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester-on-the-Severn 4 Star Hotels ![Property amenity](https://images.trvl-media.com/lodging/2000000/1780000/1770700/1770627/13f895c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/2000000/1780000/1770700/1770627/c4afc2b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1770700/1770627/ff6ead04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1780000/1770700/1770627/fb86e66b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Baltimore Washington Airport - BWI Linthicum Heights 8.8/10 Excellent (1067) "As expected for a Marriott property, the staff was friendly - the dining was good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve Louis CA $167 CA $190 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Baltimore-Hotels-The-Westin-Baltimore-Washington-Airport-BWI.h1770627.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/e94a05fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/900/846/237feb4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton Annapolis Annapolis 9.4/10 Exceptional (1012) "Staff was outstanding!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred CA $217 CA $248 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/3952dad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/d4b92367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/5575a0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis Annapolis 8.6/10 Excellent (1021) "Comfortable place to stay, nice shopping area close by. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roya CA $145 CA $165 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/26200/26137/0422878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26200/26137/1122264a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/26200/26137/087b8a1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/30000/26200/26137/69c4d9d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree Hotel Baltimore - BWI Airport Linthicum Heights 8.4/10 Very good (1302) "The stay was excellent, the room was as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracey CA $137 CA $156 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Baltimore-Hotels-DoubleTree-Hotel-Baltimore-BWI-Airport.h26137.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/04365757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/0684bd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/768e2886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Annapolis Annapolis 8.6/10 Excellent (1006) "Would stay there again very soon " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $251 CA $286 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/96000000/95350000/95349000/95348917/b84bac56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cafe](https://images.trvl-media.com/lodging/96000000/95350000/95349000/95348917/bee25c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/96000000/95350000/95349000/95348917/446923fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/96000000/95350000/95349000/95348917/463c2495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ROOST Baltimore Port Covington 9.6/10 Exceptional (336) "I love the location, staff and cleanliness. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenton CA $175 CA $206 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Baltimore-Hotels-ROOST-Baltimore.h95348917.Hotel-Information) ![Sports bar](https://images.trvl-media.com/lodging/23000000/22840000/22838000/22837995/b09687ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Massages](https://images.trvl-media.com/lodging/23000000/22840000/22838000/22837995/c4ffc9e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22840000/22838000/22837995/2160af5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Room](https://images.trvl-media.com/lodging/23000000/22840000/22838000/22837995/86e94a7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Live! Casino & Hotel - Maryland Hanover 9.0/10 Wonderful (1013) "enjoyed my stay will be back !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $245 CA $303 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Baltimore-Hotels-Live-Casino-Hotel-BaltimoreWashington-BWI-Airport.h22837995.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking, Balcony](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.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/1000000/10000/5100/5075/af281015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/fb8e8cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection Historic District 8.8/10 Excellent (872) "Clean room. Friendly staff awesome location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brent CA $285 CA $325 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b42a3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (422) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rery CA $272 CA $337 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Winchester-On-The-Severn-Annapolis-Hotels.s40-n553248635976475477-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Winchester-On-The-Severn-Annapolis-Hotels.s40-n553248635976475477-0.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Winchester-on-the-Severn. ![The Inn at Tacaro Estate](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ad846553_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Inn at Tacaro Estate 6220 Town Point Rd, Tracys Landing, MD CA $536 CA $612 total Oct 23 - Oct 24 includes taxes & fees 9.2/10 Wonderful! (10 reviews) [](https://expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester-on-the-Severn.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976475477&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976475477&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976475477&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976475477&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976475477&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976475477&star=40&star=40&amenities=WATER_PARK) 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. ## Top Winchester-on-the-Severn Hotel Reviews ![DoubleTree Hotel Baltimore - BWI Airport](//images.trvl-media.com/lodging/1000000/30000/26200/26137/0422878e_y.jpg) ### DoubleTree Hotel Baltimore - BWI Airport 10/10 Excellent "It was clean, front desk staff was friendly and helpful." [](https://expedia.ca/Baltimore-Hotels-DoubleTree-Hotel-Baltimore-BWI-Airport.h26137.Hotel-Information) ![The Westin Baltimore Washington Airport - BWI](//images.trvl-media.com/lodging/2000000/1780000/1770700/1770627/13f895c7_y.jpg) ### The Westin Baltimore Washington Airport - BWI 10/10 Excellent "As expected for a Marriott property, the staff was friendly - the dining was good. 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