Title: Book the Best Hotels with BARS in Chestertown in 2026 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chestertown Hotels with Bar ## Our top choices for Chestertown hotels with a bar ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/021b413d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/c765d8e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodge at Great Oak Landing [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) Chestertown 7.8/10 Good (77 reviews) "Very nice rooms, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephania CA $150 CA $172 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/w2069h1549x0y3-dd3dc42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Ensuite (Haven) | Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/89c7676f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/1176437a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/bb00a986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Haven Point Inn and Gallery [](https://www.expedia.ca/Rock-Hall-Hotels-Haven-Point-Inn-And-Gallery.h119027214.Hotel-Information) Rock Hall CA $207 CA $230 total includes taxes & fees Apr 21 - Apr 22 [](https://www.expedia.ca/Rock-Hall-Hotels-Haven-Point-Inn-And-Gallery.h119027214.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/5bf9cecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/052f9ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (O'Neill) | Living area](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/c3481ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Tydings)](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/727c3c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vandiver Inn [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) Havre De Grace 9.4/10 Exceptional (538 reviews) "As always we loved our stay! Definitely will be coming back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $168 CA $189 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/fafda427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/18e3859d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/1c5b9984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/3c250b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Aberdeen [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) Aberdeen 8.6/10 Excellent (643 reviews) "Quiet, clean, and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $137 CA $153 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/716a9a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/0d3003b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/d20be1bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/ad346636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Aberdeen at Ripken Stadium [](https://www.expedia.ca/Aberdeen-Hotels-Courtyard-Aberdeen-At-Ripken-Stadium.h1608237.Hotel-Information) Aberdeen 8.6/10 Excellent (227 reviews) "Room were very clean, staff were excellent and friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $129 CA $144 total includes taxes & fees Apr 19 - Apr 20 [](https://www.expedia.ca/Aberdeen-Hotels-Courtyard-Aberdeen-At-Ripken-Stadium.h1608237.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/b66763a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6cc4a825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/7e87d5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Middletown [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) Middletown 8.8/10 Excellent (889 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken CA $170 CA $188 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.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) ![Garden](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/0fbfe277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Single Room](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/ece40ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/49680cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) Stevensville 9.4/10 Exceptional (442 reviews) "Very clean room, staff was very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Byron CA $258 CA $322 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/ff957644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/74da44e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/61316540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/1bbd1ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Bel Air [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) Bel Air 9.2/10 Wonderful (257 reviews) "All staff friendly and professional " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $153 CA $171 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![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.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (728 reviews) "Clean hotel all around. Friendly stafff and comfortable environment." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jillian CA $210 CA $233 total includes taxes & fees Apr 14 - Apr 15 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1610000/1608200/1608133/e7aca489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1610000/1608200/1608133/b718c7ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1610000/1608200/1608133/ce7a79b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1610000/1608200/1608133/w4000h2664x0y0-76b9c183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn Aberdeen at Ripken Stadium [](https://www.expedia.ca/Aberdeen-Hotels-Residence-Inn-Aberdeen-At-Ripken-Stadium.h1608133.Hotel-Information) Aberdeen 9.2/10 Wonderful (112 reviews) "The staff are exceptional " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina CA $152 CA $171 total includes taxes & fees Apr 21 - Apr 22 [](https://www.expedia.ca/Aberdeen-Hotels-Residence-Inn-Aberdeen-At-Ripken-Stadium.h1608133.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-12&endDate=2026-04-13®ionId=7215&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56_y.jpg) ### Best Western Kent Narrows Inn 6/10 Okay "Breakfast was terrible and made my son and i very sick. Water pressure and temp were nonexistent and the tub clogged when showering. The tv was not working and was unplugged, which i fixed myself. When we turned on the heat the smoke detector just kept going off. Then i was told some foreign website tried to purchase extra rooms there and they wouldn't and couldnt do anything to rectify the problem." [](https://expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 6/10 Okay "The issue was the elevator was broke the whole time during every day that I’ve been there" [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/6e9faa08_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "The room was great!" [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Clean and helpful " [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/89cd8abe_y.jpg) ### Pendry Baltimore 10/10 Excellent "Great hotel!" [](https://expedia.ca/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Nice and and courteous, friendly staff very clean, great entertainment at the comedy factor and nightclub within facility great breakfast bar ." [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Hampton Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/932b25b8_y.jpg) ### Hampton Inn Baltimore/White Marsh 10/10 Excellent "Clean and quiet, with great front desk staff! It's a nice place for a memorable stay." [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreWhite-Marsh.h57004.Hotel-Information) ![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg) ### Home2 Suites by Hilton Baltimore/White Marsh 8/10 Good "Staff were receptive and courteous " [](https://expedia.ca/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Nice clean rooms and staff. Good location" [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Chestertown? ### What are the best hotels with bars in Chestertown? ### What is there to do in Chestertown? ### When is the best time to visit Chestertown? ### How can I get to Chestertown and around the area? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Belcamp ](https://www.expedia.ca/Belcamp-Hotels-Cheap-Hotels.0-0-d602125-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Belcamp ](https://www.expedia.ca/Belcamp-Hotels-Family-Hotel.0-0-d602125-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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