Title: The Best Hotels Closest to Annapolis Sailing School in Annapolis - 2026 Updated Prices | Expedia.co.uk [Holiday Rentals in Annapolis](https://expedia.co.uk/Annapolis-Holiday-Rentals.d6034082.Travel-Guide-HolidayRentals)[Flights to Annapolis](https://expedia.co.uk/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)[Annapolis Sailing School Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Annapolis-Sailing-School.d553248621532662324.Car-Hire-Guide)[Annapolis Sailing School Holidays](https://expedia.co.uk/Annapolis-Sailing-School-Annapolis.d553248621532662324.Attraction) ![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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [9 Feb - 10 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248621532662324&startDate=2026-02-09&endDate=2026-02-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [10 Feb - 11 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248621532662324&startDate=2026-02-10&endDate=2026-02-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248621532662324&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248621532662324&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Property class ## Our top choices for Annapolis Sailing School hotels ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite | Frette Italian sheets, premium bedding, memory-foam beds, free minibar](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/49daa5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/ab8d2ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/e818c666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn [](https://www.expedia.co.uk/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) Historic District, 1 mi from Annapolis Sailing School 9.4/10 Exceptional (86 reviews) "The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth £146 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.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) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/900/846/9175a19d.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) ### Graduate by Hilton Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) 1.5 mi from Annapolis Sailing School 9.4/10 Exceptional (1,006 reviews) "Room was clean, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian £134 includes taxes & fees 26 Feb - 27 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/c1b842f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/620f8cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) Historic District, 1.2 mi from Annapolis Sailing School 9.0/10 Wonderful (1,885 reviews) "Great rooms, very clean, loved our stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/676e246c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/1182dd74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/w3998h2663x2y4-cd8765a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/w3996h2664x4y0-50b1ab3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites By Marriott Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information) 1.9 mi from Annapolis Sailing School 9.0/10 Wonderful (173 reviews) "Clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David £92 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975885/0ca21efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975885/3215754a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975885/w3996h2664x4y0-0f5b2a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975885/w3998h2663x2y4-320fb9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn By Marriott Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Residence-Inn-By-Marriott-Annapolis.h100975885.Hotel-Information) 1.9 mi from Annapolis Sailing School 9.0/10 Wonderful (59 reviews) "The staff was kind and attentive. Great location and super clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi J. £106 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Residence-Inn-By-Marriott-Annapolis.h100975885.Hotel-Information) ![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be.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) ![Room, 2 Queen Beds, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe](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 | Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) Historic District, 0.8 mi from Annapolis Sailing School 8.8/10 Excellent (901 reviews) "Great location, nice and clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Micah £170 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/96f9cffa.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) ![Premium Room, 1 King Bed, City View | Premium bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/c301dc98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) 1.7 mi from Annapolis Sailing School 8.8/10 Excellent (1,001 reviews) "Great hotel love that they are pet friendly. Easy check in and valet parking staff great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert £142 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/2ee9107a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/58ff455e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Annapolis Downtown [](https://www.expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) 1.5 mi from Annapolis Sailing School 8.6/10 Excellent (1,005 reviews) "An amazing cozy place to stay during this snow storm!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) zhanna £84 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/6d339134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, City View | In-room safe, blackout curtains, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/34bda8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/a8bf1b01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/97119172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 86 State Circle - Luxury Boutique Hotel [](https://www.expedia.co.uk/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) Historic District, 1.2 mi from Annapolis Sailing School 10/10 Exceptional (3 reviews) "Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels." ![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg) Jo £214 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/1000000/300000/297100/297099/aed98da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/300000/297100/297099/8b20935c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/297100/297099/589ffa9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/300000/297100/297099/46c3234d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Annapolis [](https://www.expedia.co.uk/Edgewater-Hotels-Admiral-Suites.h297099.Hotel-Information) 4.1 mi from Annapolis Sailing School 9.4/10 Exceptional (63 reviews) "The staff was welcoming, the room was very clean and comfortable and tue pocation waa great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen £81 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Edgewater-Hotels-Admiral-Suites.h297099.Hotel-Information) ![Free daily self-service breakfast ](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/72ca553e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillow-top beds, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/4d956ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, pool loungers](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/745b6ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) 4 mi from Annapolis Sailing School 9.0/10 Wonderful (1,004 reviews) "Great location and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shana £78 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/38245561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking, Fireplace | Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/42a0faa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/19214323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Annapolis, MD [](https://www.expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) 4.6 mi from Annapolis Sailing School 9.0/10 Wonderful (1,002 reviews) "Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda £78 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/f69d8f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/cfbb67fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/c9fe9cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Annapolis by IHG [](https://www.expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) 3.9 mi from Annapolis Sailing School 8.8/10 Excellent (1,010 reviews) "Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jane £92 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/aabb28e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/fa54a5ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/180dd9f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9ee94703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Annapolis by IHG [](https://www.expedia.co.uk/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) 3.8 mi from Annapolis Sailing School 8.8/10 Excellent (204 reviews) "Hotel was clean staff was friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim £70 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillow-top beds, desk](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/c12dde92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/fbea7cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/a8e6d435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) 4.1 mi from Annapolis Sailing School 8.8/10 Excellent (985 reviews) "We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olga £76 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/c21b600a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/d4b92367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) 3.9 mi from Annapolis Sailing School 8.6/10 Excellent (1,004 reviews) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose Miguel £69 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/f531cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7f9539e1.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/f5af10f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/0a68e5bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) 4.2 mi from Annapolis Sailing School 8.6/10 Excellent (1,000 reviews) "Wonderful stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela £85 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.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) ![Dining](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/462e7c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Single Room | Frette Italian sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/ece40ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/0fbfe277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club [](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) 8.1 mi from Annapolis Sailing School 9.4/10 Exceptional (435 reviews) "Amazing rooms and service!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alicia £146 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Room, 1 King Bed, Non Smoking (Whirlpool) | In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/21b35d2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/5f8f1383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/59ba3f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/9a55b500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Annapolis by IHG [](https://www.expedia.co.uk/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information) 3.7 mi from Annapolis Sailing School 8.2/10 Very good (1,001 reviews) " The rooms where clean, staff where so helpful. The cafe with a hot bar breakfast was excellent it was always clean and replenished with Great Coffee. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherri £85 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/ff58e28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillow-top beds, in-room safe, individually furnished](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/d4347c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/e600218e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/a336329e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) 4 mi from Annapolis Sailing School 8.2/10 Very good (1,002 reviews) "Food was fresh, great verity. Staff was amazing, very nice , great customer service and amazing personalities!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mandy £75 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.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.co.uk/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24®ionId=553248621532662324&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Compare popular hotels close to Annapolis Sailing School | Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included | | | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | ----------------- | --------------------------- | ------------------ | ---- | --- | ------------ | ------------- | | | ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Flag House Inn | 3.5 star property | 9.4Exceptional86 reviews | View | | | | | | | ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Graduate by Hilton Annapolis | 4.0 star property | 9.4Exceptional1,006 reviews | View | | | | | | | ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Historic Inns of Annapolis | 3.5 star property | 9.0Wonderful1,885 reviews | View | | | | | | | ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/676e246c.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Fairfield Inn & Suites By Marriott Annapolis | 3.0 star property | 9.0Wonderful173 reviews | View | | | | | | | ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975885/0ca21efe.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Residence Inn By Marriott Annapolis | 3.0 star property | 9.0Wonderful59 reviews | View | | | | | | ## Top Annapolis Sailing School Hotel Reviews ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "The room was ready early and very clean..staff was very friendly " [](https://expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!" [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Everything! The hotel was clean, great location, and the front desk clerk was kind and helpful! " [](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "Great!!" [](https://expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Beautiful Condo - Water View Near City Dock ](https://images.trvl-media.com/lodging/34000000/33500000/33496000/33495970/w4000h2785x0y0-a6314b8c_y.jpg) ### Beautiful Condo - Water View Near City Dock 10/10 Excellent "Great spot, location, ease of access, great host communication, would stay again." [](https://expedia.co.uk/Annapolis-Hotels-Beautiful-Condo-Water-View-Near-City-Dock.h33495970.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Very welcoming and room very clean." [](https://expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Stunning Craftsman Steps to Downtown Annapolis & Spa Creek with Game Room, Parking and Backyard](https://images.trvl-media.com/lodging/96000000/95310000/95306900/95306889/db67139d_y.jpg) ### Stunning Craftsman Steps to Downtown Annapolis & Spa Creek with Game Room, Parking and Backyard 10/10 Excellent "Second year renting this great home with my family to celebrate Christmas. Amazing walkable location to Eastport and downtown Annapolis restaurants and shopping. Easy check in and host was quick to communicate with. Very family friendly. Will be back again next year to continue this new tradition." [](https://expedia.co.uk/Annapolis-Hotels-Stunning-Craftsman-Steps-To-Downtown-Annapolis-Spa-Creek-With-Game-Room.h95306889.Hotel-Information) ![Dog-Friendly Annapolis Apartment | Parking, Private Backyard & Walkable to Shops and Restaurants](https://images.trvl-media.com/lodging/105000000/104620000/104617300/104617221/784a4873_y.jpg) ### Dog-Friendly Annapolis Apartment | Parking, Private Backyard & Walkable to Shops and Restaurants 10/10 Excellent "The location was perfect for all the Christmas activities we attended. We were able to walk to all the finest food. " [](https://expedia.co.uk/Annapolis-Hotels-Walk-Everywhere-In-Annapolis-From-1st-Floor-Dog-Friendly-Apartment-With-Parking-And-Backyard.h104617221.Hotel-Information) ![Eastport Cottage .5 mi from Downtown Annapolis ](https://images.trvl-media.com/lodging/40000000/39180000/39173300/39173273/7d8ed9b6_y.jpg) ### Eastport Cottage .5 mi from Downtown Annapolis 10/10 Excellent "Wonderful 10-day stay at this Eastport cottage. We had a very enjoyable experience being close to restaurants and activities and downtown Annapolis, as well as walking around the Eastport neighborhood and playing in nearby playgrounds. The house is in great condition and has everything we needed. Would definitely return to this cottage on my next trip to the area. " [](https://expedia.co.uk/Annapolis-Hotels-Eastport-Cottage-5-Mi-From-Downtown-Annapolis.h39173273.Hotel-Information) ## Hotels near other Annapolis Sailing School attractions ![Annapolis Harbor](https://images.trvl-media.com/place/6034082/c2e7221b-185d-41c4-a25c-b4fefc7f3c5e.jpg) Photo by Michael Lore ### Susan Campbell Park Susan Campbell Park is just one of the places to see in Annapolis, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=938006365035819008) ![Ego Alley](https://images.trvl-media.com/place/553248635919228117/d5242255-2379-4ab6-a319-d8e08322225a.jpg) ### Ego Alley Explore the waterfront in Annapolis with a trip to Ego Alley. While you're here, you can savour the top-notch restaurants. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635919228117) ### Annapolis Landing Marina Explore the waterfront in Annapolis with a trip to Annapolis Landing Marina. Stroll along the riverfront or experience the area's live music. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621558039664) ### Annapolis Maritime Museum 4.6/5 (5 reviews) You can study the exhibits at Annapolis Maritime Museum, a museum with a storied past, during your travels to Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662325) ### Sparrows Beach Why not spend a lazy afternoon at Sparrows Beach during your trip to Annapolis? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635983991616) ### Annapolis Harbor Explore the waterfront in Annapolis with a trip to Annapolis Harbor. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=938006130580357120) ### Carrs Beach Why not spend a lazy afternoon at Carrs Beach during your trip to Annapolis? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635983991693) ### Kunta Kinte Plaque & Alex Haley Memorial You can find out about the history of Annapolis when you stop by Kunta Kinte Plaque & Alex Haley Memorial. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=658955797326893056) ## Frequently asked questions ### What's the area like around Annapolis Sailing School? ### What's the best place to stay near Annapolis Sailing School? ### How many hotels will I be able to find near Annapolis Sailing School? ### If I need to cancel the hotel reservation for my stay near Annapolis Sailing School, will I receive a refund? ### What can I see and do near Annapolis Sailing School?