Title: Hotels in Chester, MD - Best Chester Hotels from £53 - Fully Refundable Options - Expedia.co.uk [Holiday Rentals in Chester](https://expedia.co.uk/Chester-Holiday-Rentals.d3000440455.Travel-Guide-HolidayRentals)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d3000440455.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d3000440455.Holidays-City-Breaks) ![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2/sunset-fishing-charter-boat-docked-at-marina-harbor-bridge.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr # Find hotels in Chester, MD from £53 - ![](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 ## Go beyond your typical stay in Chester Spa [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&amenities=SPA_ON_SITE) Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&amenities=POOL) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&lodging=APARTMENT) Sea view [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&amenities=OCEAN_VIEW) House­boat [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&lodging=HOUSE_BOAT) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&amenities=HOT_TUB) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&travelerType=family_friendly) Cottage [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&lodging=COTTAGE) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&amenities=PETS) Condo [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&lodging=CONDO) Waterpark [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&amenities=WATER_PARK) ## Check prices for these dates Tonight [2 Dec - 3 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2025-12-02&endDate=2025-12-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [3 Dec - 4 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2025-12-03&endDate=2025-12-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 10 Chester hotels and places to stay ![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) ![Suite, 1 Bedroom | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG Grasonville 9.2/10 Wonderful (928) "nice, clean, up to date, budget friendly hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mike £66 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a.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/2000000/1230000/1222200/1222176/66a1e121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina Grasonville 9.0/10 Wonderful (1010) "Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta £93 includes taxes & fees 8 Dec - 9 Dec [](https://www.expedia.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/bdf87bb6.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) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/e60ed5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina Grasonville 9.4/10 Exceptional (668) "Great view, good ambiance all around" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dianne £97 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.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) ![Premium bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/5575a0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.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) ### DoubleTree by Hilton Hotel Annapolis Annapolis 8.6/10 Excellent (1041) "room was clean and quiet; parking was easy and safe. Very good welcome cookies too." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Francisco £53 includes taxes & fees 21 Dec - 22 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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) ![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) ![Business centre](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/a77fa217.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) ### The Westin Annapolis Annapolis 8.6/10 Excellent (1007) "Great environment" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Salvador E £131 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.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) ![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) ![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/cfbb67fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Annapolis by IHG Annapolis 8.8/10 Excellent (1016) "Clean, easy parking, nice staff but over priced breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabrielle £92 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Premium bedding, pillow-top beds, in-room safe, individually furnished](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/ff58e28e.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 Annapolis 8.2/10 Very good (1010) "I had a great experience at my stay at Hampton " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Idris O £78 includes taxes & fees 8 Dec - 9 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/f531cd56.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7f9539e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Annapolis Annapolis 8.6/10 Excellent (1003) "Wonderful stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela £83 includes taxes & fees 21 Dec - 22 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ![Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/9e6dd0ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Annapolis, MD Annapolis 9.0/10 Wonderful (1015) "Clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jodi £72 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![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) ![Deluxe Room, 2 Queen Beds | Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/f68fafe7.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, 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 Historic District 8.8/10 Excellent (878) "Clean room. Friendly staff awesome location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brent £126 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.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) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort Stevensville 9.2/10 Wonderful (127) "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 £116 includes taxes & fees 7 Dec - 8 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.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 Historic District 9.0/10 Wonderful (1912) "Excellent hotel Really nice staff Love the valet guys " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ben [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hypo-allergenic bedding, down duvets, 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) ![Reception](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/9ddea0cd.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) ![Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/6281ec00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Annapolis Annapolis 8.2/10 Very good (1002) "I had a lovely stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kalynn £56 includes taxes & fees 21 Dec - 22 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information) ![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) ![Deluxe Room, 2 Queen Beds, Accessible (Hearing) | In-room safe, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/aeb43618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f.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 Annapolis 8.6/10 Excellent (1013) "Clean room, great staff, great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susanne £68 includes taxes & fees 1 Jan - 2 Jan 2026 [](https://www.expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![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, 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) ![Room amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/9a55b500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/d39579fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Annapolis by IHG Annapolis 8.2/10 Very good (1004) "Clean room and friendly staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Silvia £65 includes taxes & fees 19 Dec - 20 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information) ![Egyptian cotton sheets, premium bedding, pillow-top beds, desk](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/6846c015.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) ![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) ### Sonesta ES Suites Annapolis Edgewater 8.8/10 Excellent (960) "Nice breakfast, clean room, great parking" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy £71 includes taxes & fees 21 Dec - 22 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/ac9f5b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/cea7f239.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/2000000/1370000/1364100/1364028/08fc01db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Annapolis Annapolis 9.0/10 Wonderful (1004) "Friendly staff and comfortable rooms. We love staying here when we visit the area as a family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer £87 includes taxes & fees 7 Dec - 8 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.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) ![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) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/d2860230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (429) "Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Warren £173 includes taxes & fees 7 Dec - 8 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Outdoor banquet area](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/w2877h1800x0y0-f772721c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/ee1a612d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Double Queen First Level - Dog Friendly | View from room](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/0c190249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/b30d5f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tilghman Island Inn Tilghman 9.6/10 Exceptional (119) "Great room and water view! Staff is very friendly and welcoming. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole £166 includes taxes & fees 7 Dec - 8 Dec [](https://www.expedia.co.uk/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.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) ![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) ### Graduate by Hilton Annapolis Annapolis 9.4/10 Exceptional (1010) "Nice big rooms, comfortable beds. Well maintained. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret £105 includes taxes & fees 21 Dec - 22 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.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=2025-12-16&endDate=2025-12-17®ionId=3000440455&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=HTG_BF_PROMO_3000440455) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d3000440455.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d3000440455.Travel-Guide-Hotels) ## Stay near popular Chester attractions [](https://www.expedia.co.uk/Chesapeake-Exploration-Center-Hotels.0-l553248621561879491-0.Travel-Guide-Filter-Hotels) ### Chesapeake Exploration Center Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561879491) ## Learn more about Chester Chester awaits: its island views, sunny weather, golf and more! [See all hotels in Chester](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-16&endDate=2025-12-17&adults=2®ionId=3000440455) ![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=900&h=547&p=1&q=high) Photo by Patricia Knorr ## Top Chester Hotel Reviews ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "room was clean and quiet; parking was easy and safe. Very good welcome cookies too." [](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Comfy beds, helpful staff" [](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.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 "Great location and customer care " [](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Hilton Garden Inn Kent Island Marina](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a_y.jpg) ### Hilton Garden Inn Kent Island Marina 10/10 Excellent "Amazing location. Clean and well kept. " [](https://expedia.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.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 "clean and great location" [](https://expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "roomy and spacious" [](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "I have stayed several times over the last month or so totaling at leadt 7 nights and during every stay i have had a great experiene. Particularly with Chrissy who ive seen maonly during the night shift. Cannot understate how helpful and pleasant she has been. Probably the reason i wont stay anywhere else(if theres availability) in and around the Annapolis area. Keep up the amazing customer service!! 5 STARS " [](https://expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160_y.jpg) ### Best Western Kent Narrows Inn 10/10 Excellent "Great Customer Service, Clean Room I Will Recommend it 1000000000000%" [](https://expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Best Western Annapolis](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Nice clean room. Good breakfast. Ample free parking." [](https://expedia.co.uk/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ## More cheap stays in Chester ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### St Michaels Inn 1228 S Talbot Street St. Michaels MD £86 29 Dec - 30 Dec includes taxes & fees 8/10 Very Good! (1,005 reviews) [](https://expedia.co.uk/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Best Western Annapolis](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Annapolis 2520 Riva Rd Annapolis MD £57 7 Dec - 8 Dec includes taxes & fees 7.6/10 Good! (1,009 reviews) [](https://expedia.co.uk/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Annapolis 124 Womack Dr Annapolis MD £78 8 Dec - 9 Dec includes taxes & fees 8/10 Very Good! (1,008 reviews) [](https://expedia.co.uk/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Candlewood Suites Annapolis by IHG 1 Womack Dr Annapolis MD £68 19 Dec - 20 Dec includes taxes & fees 8.8/10 Excellent! (171 reviews) [](https://expedia.co.uk/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Kent Narrows Inn 3101 Main Street Grasonville MD £70 8 Dec - 9 Dec includes taxes & fees 8/10 Very Good! (1,005 reviews) [](https://expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 8523 Ocean Gtwy Easton MD £67 14 Dec - 15 Dec includes taxes & fees 7.6/10 Good! (821 reviews) [](https://expedia.co.uk/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) ## Frequently asked questions ### Where can I find the best nightlife in Chester? > Chester is a charming area with a laid-back atmosphere, but when it comes to nightlife, options are somewhat limited. > > > > However, nearby Annapolis, just a short drive away, boasts a vibrant nightlife scene that's well worth the visit. In Annapolis, the historic downtown area features bustling bars and live music venues along West Street, where you can enjoy everything from casual pubs to upscale lounges. > > > > For those who enjoy a lively waterfront experience, the area around Ego Alley is superb for sipping cocktails while watching boats glide by. If you're searching for a relaxed evening, consider heading to the local breweries or wine bars that often host events and tastings. ### Can I cancel my hotel reservation on Expedia? > You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester. ### How can I save on a Chester hotel booking with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Chester hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings. ### How much is the nightly rate at a Chester hotel? > Prices for hotels in Chester often vary, but you can find a great deal from £53 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate. ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [2 Star Hotels in Kent Island](https://www.expedia.co.uk/2Star-Kent-Island-Hotels.s20-0-d553248635077608788.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Gibson Island](https://www.expedia.co.uk/5Star-Gibson-Island-Hotels.s50-0-d3000347885.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Kent Island](https://www.expedia.co.uk/5Star-Kent-Island-Hotels.s50-0-d553248635077608788.Travel-Guide-Filter-Hotels) - [Hotels near Annapolis City Dock](https://www.expedia.co.uk/Annapolis-City-Dock-Hotels.0-l553248633992240262-0.Travel-Guide-Filter-Hotels) - [Accor Hotels in Annapolis](https://www.expedia.co.uk/Annapolis-Hotels-Accor-Hotels.0-0-d6034082--bAccorHotels.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Annapolis](https://www.expedia.co.uk/Annapolis-Hotels-Beach-Hotels.0-0-d6034082-tBeachHotels.Travel-Guide-Filter-Hotels) - 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