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/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Chestertown, MD from CA $109 - ![](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 ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.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) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (940) "It was very comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $108 CA $120 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![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/c38ba9d1.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6a6a4995.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 (866) "Amazing stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katiana CA $130 CA $144 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/3c250b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/88d1de79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/fafda427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/36fcefa1.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 (634) "Close to restaurants, friendly staff, nice room, food was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peggy CA $132 CA $147 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) ![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) ![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) ![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/72a73d25.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) "Very nice rooms, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephania CA $135 CA $155 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/f6ab6350.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/2000000/1610000/1608300/1608237/6f1191b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/2000000/1610000/1608300/1608237/6b59ba72.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 (219) "We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $115 CA $129 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Courtyard-Aberdeen-At-Ripken-Stadium.h1608237.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/78000000/77980000/77974900/77974873/9e72db94.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) ![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 (680) "The staff are the absolute best. Our room was perfect." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $159 CA $176 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/6428fe21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/b385545e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/b77a7385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Baltimore/White Marsh [](https://www.expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) Nottingham 7.8/10 Good (1005) "Very nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina CA $144 CA $166 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.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/e17d8d11.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) Grasonville 9.0/10 Wonderful (1000) "Clean and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $156 CA $173 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/898500/898446/86a9f017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/900000/898500/898446/840fad18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible (Additional Living Area)](https://images.trvl-media.com/lodging/1000000/900000/898500/898446/47917a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/900000/898500/898446/e7c2a28a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Belcamp - Aberdeen Area by IHG [](https://www.expedia.ca/Belcamp-Hotels-Holiday-Inn-Belcamp-Aberdeen-Area.h898446.Hotel-Information) Belcamp 8.4/10 Very good (741) "the room was spotless and the breakfast was very nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carl CA $97 CA $109 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Belcamp-Hotels-Holiday-Inn-Belcamp-Aberdeen-Area.h898446.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/a4c59418.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) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/1f3f9838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/71bdd057.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 (234) "Wonderful staff! So nice, clean and comfortable. Will definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $133 CA $149 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.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=2026-01-10&endDate=2026-01-11®ionId=7215&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg) ### Americas Best Value Inn Edgewood 10/10 Excellent "Quiet and clean " [](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "The chef was amazing" [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.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 "Best place to stay is the main building" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 10/10 Excellent "Muy buenos " [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.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 "Lovely hotel, my favorite place to stay in Annapolis!" [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Yes and yes" [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Very nice" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.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 "Always a pleasure dealing with Best Western!!" [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "Really nice cozy room we had the terrace balcony would definitely stay again!" [](https://expedia.ca/Baltimore-Hotels-Pendry-Baltimore.h17395897.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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