Title: TOP 10 Hotels in Chester, MD (from $90) - COMPETITIVE PRICES | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx3000440455)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d3000440455.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d3000440455.Destination-Travel-Guides) ![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=1200&h=500&q=medium) Photo by Patricia Knorr ![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/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 Ocean view [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=OCEAN_VIEW) Great for families [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&travelerType=family_friendly) Spa [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=SPA_ON_SITE) Pool [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=POOL) Hot tub [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=HOT_TUB) Pet-friendly [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=PETS) Apart­ment [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&lodging=COTTAGE) Condo [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&lodging=CONDO) Waterpark [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=WATER_PARK) ## Check prices for these dates Tonight [Feb 9 - Feb 10](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-02-09&endDate=2026-02-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 10 - Feb 11](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-02-10&endDate=2026-02-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/30dd84ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.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) ### Hyatt Place Kent Narrows & Marina [](https://www.expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (712 reviews) "Amazing location and staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi J. $118 nightly $131 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop 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) ![Reception](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/0c127689.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) ### SpringHill Suites by Marriott Annapolis [](https://www.expedia.com/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) Annapolis 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 $93 nightly $106 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/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 drapes, 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) ![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 [](https://www.expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) Annapolis 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 $94 nightly $107 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/d4b92367.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) ![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) ### DoubleTree by Hilton Hotel Annapolis [](https://www.expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) Annapolis 8.6/10 Excellent (1,004 reviews) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose Miguel $83 nightly $94 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/8fe1f1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Annapolis by IHG [](https://www.expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) Annapolis 8.8/10 Excellent (1,010 reviews) "Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jane $110 nightly $125 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/fbea7cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/4dfe2462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/c12dde92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Annapolis [](https://www.expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) Edgewater 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 $91 nightly $104 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Room, 1 King Bed, Non Smoking (Whirlpool) | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/21b35d2a.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/5f8f1383.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.com/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information) Annapolis 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 $101 nightly $115 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.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 drapes, 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.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) Annapolis 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 $96 nightly $109 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/48975360.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) ### Graduate by Hilton Annapolis [](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) Annapolis 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 $161 nightly $183 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/c52c5ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/ec18bd5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/3a599b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Easton Inn & Suites [](https://www.expedia.com/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) Easton 9.2/10 Wonderful (1,001 reviews) "Nice friendly staff, clean room and lobby" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joi $119 nightly $131 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/8260c7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/97742239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/d2bab96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/w1504h992x0y8-f18eeee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Easton [](https://www.expedia.com/Easton-Hotels-Hampton-Inn-Easton.h1432437.Hotel-Information) Easton 9.0/10 Wonderful (559 reviews) "all excellent with kudos to staff and the breakfast cook." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOSEPH $110 nightly $121 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Easton-Hotels-Hampton-Inn-Easton.h1432437.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 | In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/4973a39f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/7b97c3b5.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) ### Quality Inn Grasonville near Kent Island [](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) Grasonville 7.8/10 Good (869 reviews) "Nice staff and rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter $84 nightly $93 total Feb 11 - Feb 12 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![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, sun loungers](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/6281ec00.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/9ddea0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Annapolis [](https://www.expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information) Annapolis 8.2/10 Very Good (1,002 reviews) "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 $85 nightly $97 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.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) ![Restaurant](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/97b0db53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites By Marriott Annapolis [](https://www.expedia.com/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information) Annapolis 9.0/10 Wonderful (173 reviews) "Clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David $110 nightly $125 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.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) ![Premium Room, 1 King Bed, City View | Premium bedding, pillowtop 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) ![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/2000000/1680000/1678800/1678710/0684bd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Annapolis [](https://www.expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) Annapolis 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 $169 nightly $193 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7f9539e1.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.com/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) Annapolis 8.6/10 Excellent (1,000 reviews) "Wonderful stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela $101 nightly $115 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/24fa7509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (959 reviews) "Lovely location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl $112 nightly $124 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/1d7c16b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/bb752da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn [](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) Grasonville 8.0/10 Very Good (1,001 reviews) "Nice breakfast, cleanroom. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne $83 nightly $93 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/4e51f020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/21c5252e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/e0e2d461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn [](https://www.expedia.com/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) Easton 7.6/10 Good (841 reviews) "Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer $85 nightly $94 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/391fbabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/4be52931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/d6387655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/11cbce69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wildset [](https://www.expedia.com/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) Downtown St. Michaels 9.8/10 Exceptional (417 reviews) "Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred $219 nightly $241 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/St-Michaels-Hotels-The-Wildset.h64410566.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.com/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24®ionId=3000440455&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d3000440455.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d3000440455.Travel-Guide-Hotels) ## Stay near popular Chester attractions ### Chesapeake Exploration Center Learn about the events happening at 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.com/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.com/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24&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 ![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 "Clean room. Friendly staff. Good food. " [](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![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.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![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 spotless. Staff was very courteous. Would highly recommended." [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 "The room was very spacious. Staff were nice. Amenities were excellent. Good location for our stay." [](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.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 "We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️" [](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Holiday Inn Express & Suites Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/59ba3f76_y.jpg) ### Holiday Inn Express & Suites Annapolis by IHG 10/10 Excellent "Yes." [](https://expedia.com/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.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.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Room was nice, quiet, clean. Great for a stay-cation on the wateefront" [](https://expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg) ### Hampton Inn & Suites Annapolis 10/10 Excellent "The staff here was absolutely amazing. They went above and beyond to get me anything I needed during the snowstorm. The rooms are also very nice. Highly recommend and will return!! " [](https://expedia.com/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ## More cheap stays in Chester ![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 $79 nightly $90 total Feb 22 - Feb 23 Total with taxes and fees 7.6/10 Good! (1,000 reviews) [](https://expedia.com/Annapolis-Hotels-Best-Western-Annapolis.h2882.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 $83 nightly $93 total Feb 16 - Feb 17 Total with taxes and fees 8/10 Very Good! (1,000 reviews) [](https://expedia.com/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 $85 nightly $94 total Feb 16 - Feb 17 Total with taxes and fees 7.6/10 Good! (837 reviews) [](https://expedia.com/Easton-Hotels-Quality-Inn.h11364.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 $84 nightly $96 total Feb 15 - Feb 16 Total with taxes and fees 8.8/10 Excellent! (203 reviews) [](https://expedia.com/Annapolis-Hotels-Homestyle-Suites.h1160798.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 $89 nightly $102 total Mar 1 - Mar 2 Total with taxes and fees 8/10 Very Good! (1,001 reviews) [](https://expedia.com/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![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 $103 nightly $114 total Feb 16 - Feb 17 Total with taxes and fees 8/10 Very Good! (1,000 reviews) [](https://expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ## Hotels in Chester with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 3 properties [](https://expedia.com/5Star-Chester-Hotels.s50-0-d3000440455.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 6 properties [](https://expedia.com/4Star-Chester-Hotels.s40-0-d3000440455.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 78 properties [](https://expedia.com/3Star-Chester-Hotels.s30-0-d3000440455.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 102 properties [](https://expedia.com/2Star-Chester-Hotels.s20-0-d3000440455.Travel-Guide-Filter-Hotels) ## Find out more about Chester ### Top reasons to visit Chester - **Outdoor Adventures:** Chester offers a variety of outdoor activities, including golfing, marinas, and urban parks, perfect for family fun. - **Beautiful Beaches:** Enjoy sandy shores and scenic views, ideal for relaxation and beach vacations. - **Local Nightlife:** Experience the community's essence at local bars and restaurants, showcasing unique flavors and atmosphere. - **Charming Accommodations:** Find a range of lodging options, from pet-friendly hotels to cozy bed and breakfasts. - **Nearby Attractions:** Explore surrounding cities and neighborhoods rich in history and culture for a complete getaway experience. ### Find great hotels near Chester Explore the delightful hotel accommodations in Chester, Maryland, perfect for your getaway. Whether you're looking for pet-friendly options, family-friendly environments, or business-themed stays, Chester offers a variety of hotels and charming bed and breakfasts. With numerous hotel reviews available, you can easily find the best lodging that suits your needs for a memorable vacation experience. - **[Historic Inns of Annapolis: ](https://www.expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)** Experience a blend of rich history and modern comfort at the Historic Inns of Annapolis. Located 11 miles from Chester, this charming 3.5-star hotel is perfect for business travelers and families alike. The property features well-equipped meeting rooms and versatile conference spaces, catering to your professional needs. Families will appreciate the child-friendly amenities, including free cribs and a welcoming atmosphere. With its quaint architecture and central location, it also serves as an excellent base for exploring Annapolis's cultural heritage. - **Country Inn & Suites by Radisson, Annapolis, MD:** This 3-star hotel, situated 14 miles from Chester, offers a warm and inviting environment ideal for both business and leisure travelers. The Country Inn & Suites by Radisson is pet-friendly and LGBTQIA welcoming, ensuring a comfortable stay for all guests. Enjoy convenient business amenities, including a 24-hour accessible business center and multiple meeting rooms. The hotel also features a dedicated dog exercise area, making it perfect for pet owners. Relax in cozy accommodations designed for a homely feel, and take advantage of its close proximity to Annapolis attractions. - **[Graduate by Hilton Annapolis: ](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)** Located 11 miles from Chester, the Graduate by Hilton Annapolis is a stylish 4-star hotel that caters to business travelers and pet owners while embracing LGBTQIA inclusivity. The hotel’s vibrant atmosphere and unique decor reflect the local culture, providing an engaging experience. Business amenities such as meeting rooms and conference spaces are readily available for your professional needs. Guests traveling with pets will find comfort in knowing that they are welcome, with provisions for food and water bowls. This hotel promises a memorable stay with its blend of comfort, convenience, and character. ### Where to stay near Chester Discover the charm of Chester, Maryland, where outdoor adventures and family-friendly activities await. This picturesque destination on the Eastern Shore offers sunny weather and a welcoming atmosphere, perfect for a memorable getaway. Explore nearby cities and neighborhoods that showcase rich history, relaxation, and friendly faces. Whether you're seeking a beach vacation or a tranquil retreat, Chester has something for everyone to enjoy on their family getaway. - **[Annapolis: ](https://www.expedia.com/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)** Located 11 miles from Chester, Annapolis is a charming city known for its rich maritime history and vibrant atmosphere. This city attracts visitors year-round, with peak travel times from May to July. Annapolis offers a delightful blend of family-friendly activities, outdoor adventures, and city experiences. Visitors can explore its historic academy, relax by the beach or lake, and indulge in shopping at its local mall centers. The picturesque waterfront and historic streets make it an ideal destination for both relaxation and exploration. - **[Stevensville: ](https://www.expedia.com/Stevensville-Hotels.d162393.Travel-Guide-Hotels)** Just 1 mile from Chester, Stevensville is a quaint city that offers a perfect getaway for families and outdoor enthusiasts. The travel experience here is moderately seasonal, with peak visits in April and from June to July. Stevensville is renowned for its beautiful scenery and recreational areas, including a scenic boardwalk that invites leisurely strolls. Nearby landmarks like the beach and national state park provide ample opportunities for outdoor activities, making it a fantastic spot for those looking to connect with nature while enjoying local shopping centers. - **[Kent Narrows: ](https://www.expedia.com/Kent-Narrows-Hotels.d553248635077720315.Travel-Guide-Hotels)** A charming village located 3 miles from Chester, Kent Narrows offers a romantic and family-friendly atmosphere. With travel peak times from June to August, this destination is perfect for summer outings. Visitors can explore the vibrant boardwalk, enjoy shopping at local centers, and discover stunning natural features like the nearby beach and national state park. The esplanade offers scenic views and opportunities for relaxation, making Kent Narrows a delightful choice for those seeking both adventure and tranquility. ### Things to do near Chester Chester, Maryland is perfect for outdoor family and beach vacations, offering a range of activities like golfing and exploring recreational areas. Visitors can enjoy scenic golf courses and experience the area's natural beauty. For nightlife, check out local bars and restaurants that capture the essence of the community. Overall, Chester provides a blend of relaxation and adventure, making it an ideal destination for a memorable getaway. **Shopping** In Chester, visit [Paul Reed Smith Guitars](https://www.expedia.com/Paul-Reed-Smith-Guitars-Hotels.0-l747757786500468736-0.Travel-Guide-Filter-Hotels), just 2 miles away for unique gifts. [Queenstown Premium Outlets](https://www.expedia.com/Queenstown-Premium-Outlets-Hotels.0-l553248621532662352-0.Travel-Guide-Filter-Hotels), 7 miles away, offers a variety of shops and family-friendly entertainment. If you're up for a drive, check out [Annapolis Harbour Center](https://www.expedia.com/Annapolis-Harbour-Center-Hotels.0-l553248621561879652-0.Travel-Guide-Filter-Hotels), located 14 miles away, for more shopping and dining options. **Recreation** Experience the energetic atmosphere at [Navy-Marine Corps Memorial Stadium](https://www.expedia.com/Navy-Marine-Corps-Memorial-Stadium-Hotels.0-l6091645-0.Travel-Guide-Filter-Hotels), just 12 miles away, where you can enjoy various sporting events. For a tranquil day, head to [Queenstown Harbor Golf Club](https://www.expedia.com/Queenstown-Harbor-Golf-Club-Hotels.0-l6091731-0.Travel-Guide-Filter-Hotels), 7 miles away, and immerse yourself in nature while playing a round of golf amidst beautiful landscapes. **Adventure** Experience the thrill of sailing at [Annapolis Sailing School](https://www.expedia.com/Annapolis-Sailing-School-Hotels.0-l553248621532662324-0.Travel-Guide-Filter-Hotels), located 10 miles from Chester, where outdoor sports meet adventure on the water. For family fun, visit [Chesapeake Beach Water Park](https://www.expedia.com/Chesapeake-Beach-Water-Park-Hotels.0-l553248621532662257-0.Travel-Guide-Filter-Hotels), 24 miles away, offering exciting rides and entertainment. Enjoy scenic views while hiking on the [B&A Trail](https://www.expedia.com/BA-Trail-Hotels.0-l553248621532662355-0.Travel-Guide-Filter-Hotels), 17 miles from Chester. **Nightlife** Experience the vibrant nightlife in Chester by visiting [The Colonial Players](https://www.expedia.com/The-Colonial-Players-Hotels.0-l553248621532662280-0.Travel-Guide-Filter-Hotels) for a captivating theater performance, or unleash your competitive spirit at [Annapolis Bowl](https://www.expedia.com/Annapolis-Bowl-Hotels.0-l553248621532662328-0.Travel-Guide-Filter-Hotels)'s arcadeAdventureZone. For more entertainment, check out [Avalon Theatre](https://www.expedia.com/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) for a delightful family-friendly show. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Chester To save money on your trip to Chester, plan your visit between December and February for lower accommodation rates. Consider booking your stay on a Monday, the least expensive day, and avoid Saturdays when prices peak. Use Expedia to compare prices and consider package deals that combine flights, hotels, and activities for additional savings. Join the One Key membership for exclusive discounts and earn OneKeyCash for future bookings. Look for free activities and explore the town on foot to cut transportation costs and enhance your experience. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chester is Monday. The most expensive day to stay in Chester is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals, make sure to sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Chester with your flights and activities through an Expedia package deal. - **Become a One Key member:** Join [Expedia's One Key membership](https://www.expedia.com/welcome-one-key) program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels. ### Find the best attractions near Chester Chester, Maryland, is perfect for outdoor and family beach vacations, offering a variety of attractions such as urban parks, marinas, and sandy shores. Visitors can enjoy a blend of outdoor activities and cultural experiences while exploring the area. For an unforgettable stay, consider checking out the best resorts and nearby attractions that showcase the charm of Chester and its surroundings. - **[U.S. Naval Academy: ](https://www.expedia.com/US-Naval-Academy-Hotels.0-l6077390-0.Travel-Guide-Filter-Hotels)** A historic institution located 11 miles from Chester, the U.S. Naval Academy offers a glimpse into military tradition and training. Visitors can explore its stunning architecture and scenic grounds, steeped in naval history. - **[Chesapeake Bay Bridge: ](https://www.expedia.com/Chesapeake-Bay-Bridge-Hotels.0-l6077400-0.Travel-Guide-Filter-Hotels)** This iconic modern bridge, situated 7 miles away, connects the Eastern and Western shores of Maryland. It's not only a vital transportation link but also a beautiful architectural landmark that provides breathtaking views of the bay. - **[Sandy Point State Park: ](https://www.expedia.com/Sandy-Point-State-Park-Hotels.0-l6163398-0.Travel-Guide-Filter-Hotels)** Located 7 miles from Chester, this national park is perfect for outdoor enthusiasts. With its adventure activities, scenic landscapes, and opportunities for recreation along the shoreline, it's a fantastic destination for nature lovers. ### Best time to go to Chester The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 35.1°F (1.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 37.4°F (3.0°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 43.9°F (6.6°C) | Light Rain | Mostly Sunny | Average | Average | | April | 54.1°F (12.3°C) | Light Rain | Mostly Sunny | Average | Average | | May | 63.5°F (17.5°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 72.3°F (22.4°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 77.9°F (25.5°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 76.3°F (24.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | September | 70.5°F (21.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | October | 60.3°F (15.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 48.7°F (9.3°C) | Light Rain | Mostly Sunny | Average | Average | | December | 41.0°F (5.0°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Chester Traveling to Chester, Maryland, is convenient with several major airports nearby. Washington, DC ([DCA](https://www.expedia.com/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels)\-Ronald Reagan Washington National) is about 41 miles away, with excellent hotels such as the 5-star InterContinental Washington D.C. - The Wharf and [Riggs Washington DC](https://www.expedia.com/Washington-Hotels-Riggs-Washington-DC.h37192042.Hotel-Information), both within 3 miles of the airport. Baltimore, MD ([BWI](https://www.expedia.com/Baltimore-Washington-Intl-Thurgood-Marshall-Airport-Hotels.0-aBWI-0.Travel-Guide-Filter-Hotels)\-Baltimore Washington Intl. Thurgood Marshall) is closer at 25 miles, featuring the luxurious [Sagamore Pendry Baltimore](https://www.expedia.com/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) and [Four Seasons Hotel Baltimore](https://www.expedia.com/Baltimore-Hotels-Four-Seasons-Hotel-Baltimore.h4603198.Hotel-Information), both offering airport shuttle services. Lastly, Easton, MD ([ESN](https://www.expedia.com/Easton-Newnam-Airport-Hotels.0-aESN-0.Travel-Guide-Filter-Hotels)\-Easton - Newnam) is just 17 miles away, with the 5-star [Inn at Perry Cabin](https://www.expedia.com/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) and [Inn at 202 Dover](https://www.expedia.com/Easton-Hotels-Inn-At-202-Dover.h5308723.Hotel-Information) nearby, making it easy to find comfortable accommodations. ## Frequently asked questions ### What is the best area to stay in Chester? > This area is the commercial hub of Chester, situated directly on the water where the Kent Narrows Bridge connects Kent Island to the mainland. You'll find a selection of hotels, waterfront restaurants, and marinas here. It's a practical base for exploring the Chesapeake Bay area. > > > For couples looking for a relaxing getaway, staying near the Kent Narrows is ideal. Many hotels in this area offer views of the water, and you can easily enjoy a meal at a waterfront restaurant or take a stroll along the docks. The convenience of having dining and water activities within walking distance makes for a stress-free trip. > > > Families will also find the Kent Narrows area suitable due to the range of dining choices and easy access to activities. Some hotels offer amenities like outdoor pools, and the proximity to the water provides opportunities for boat tours or fishing charters. ### When is the best time to go to Chester? > These months offer comfortable temperatures for exploring the outdoors and enjoying the Chesapeake Bay. You'll find fewer visitors compared to the peak summer months, making it easier to enjoy local attractions, dining, and scenic drives. Spring brings blooming flowers, while fall showcases colorful foliage, creating beautiful backdrops for your visit. > > > For those looking to enjoy water activities, the summer months (June-August) are ideal. While it's the busiest time, the warm weather is superb for boating, fishing, and swimming. Many local events and outdoor festivals also take place during this period, offering a lively experience. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Chester hotel booking with Expedia? > \*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo. ### How much is the nightly rate at a Chester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Washington Hotels ](https://www.expedia.com/Washington-Hotels.d178318.Travel-Guide-Hotels) - [Stevensville Hotels ](https://www.expedia.com/Stevensville-Hotels.d162393.Travel-Guide-Hotels) - [Hotel Wedding Venues Hotels in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Wedding-Hotels.0-0-d162393-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Marriott-Hotels-Resorts.0-0-d162393--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Extended Stay America Hotels in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Extended-Stay-America.0-0-d162393--bExtendedStayAmerica.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Romantic-Hotel.0-0-d162393-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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