Title: Book the Best Hotels with BARS in Chestertown in 2025 | 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) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Find Hotels with Bar in Chestertown, MD from CA $123 - ![](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 ## Top Chestertown Hotels with Bar ![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) ![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) ![Room, 1 King Bed with Sofa bed, Marina View](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/3449c94b.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 Chestertown 7.8/10 Good (72) "For the price off season the room should have had better amenities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $138 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6a6a4995.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) ![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) ### Hampton Inn Middletown Middletown 8.8/10 Excellent (847) "Enjoyed the amenities and great location for shops nearby " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $147 CA $163 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/ac399738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/59760786.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/aeda68aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/418b3837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites Baltimore White Marsh/Middle River Middle River 9.0/10 Wonderful (757) "Staff was awesome" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audrey CA $171 CA $198 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.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 Grasonville 9.2/10 Wonderful (912) "Excellent, pet friendly, clean, convenient, and beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $110 CA $123 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.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) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/716a9a4a.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) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/7061f83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Aberdeen at Ripken Stadium Aberdeen 8.6/10 Excellent (214) "The staff was very friendly, easy and quick check-in. I would chose thus hotel again, very quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna CA $118 CA $132 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Aberdeen-Hotels-Courtyard-Aberdeen-At-Ripken-Stadium.h1608237.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) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/36fcefa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/6380c7ac.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) ### Hilton Garden Inn Aberdeen Aberdeen 8.6/10 Excellent (629) "Terrific service, cool clean room with blackout shades. Slept like a baby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cornelia CA $135 CA $151 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.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) ![Meeting facility](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/96859422.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) ### Hilton Garden Inn Bel Air Bel Air 9.2/10 Wonderful (217) "The staff was amazing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kendra CA $143 CA $161 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86.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) ![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) ### Hyatt Place Kent Narrows & Marina Grasonville 9.4/10 Exceptional (642) "Great location and rooms. Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ana CA $189 CA $210 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.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) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1871) "Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine [](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (423) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rery CA $259 CA $323 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.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=2025-11-14&endDate=2025-11-15®ionId=7215&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Friendly and welcoming valet and front desk. Beautiful and clean rooms. Disappointed no restaurant but understand. " [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](//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 "I liked the breakfast because it had cold stuff. And good hot food. Eggs Sausage waffles and juice. " [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Lovely room" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Best Western Plus Hotel & Conference Center](//images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef or turkey bacon would’ve been better options . The hotel was clean , security was phenomenal especially during event times keeping hotel guest secure. I would definitely stay here again " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Garner Hotel Glen Burnie BWI Airport Area by IHG](//images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2_y.jpg) ### Garner Hotel Glen Burnie BWI Airport Area by IHG 10/10 Excellent "Will definitely be back again 🙌" [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](//images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "On arrival we met Catalina on reception. An extremely pleasant and helpful girl. After that our stay was very comfortable." [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Americas Best Value Inn Edgewood](//images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg) ### Americas Best Value Inn Edgewood 10/10 Excellent "Staff" [](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Comfort Inn & Suites Chestertown](//images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Everything was great - the beds and pillows are very comfortable, room very clean and breakfast was decent and staff very friendly. " [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "Love it always " [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Chestertown? > Chestertown features 37 hotels and other accommodations to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you're here, consider a visit to Historical Society of Kent County Maryland and Rolphs Wharf Marina. ### What are the best hotels with bars in Chestertown? > Here are some favorite hotels with bars in and around Chestertown: [Red Roof Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information): Lodge with restaurant. Enjoy the 3 bars, free WiFi, and free parking. [Comfort Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information): Enjoy the bar, free WiFi, and room service. [The Lodge at Great Oak Landing](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Historic Inns of Annapolis](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information): Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. [Hilton Garden Inn Baltimore/White Marsh](https://www.expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information): Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool. ### What is there to do in Chestertown? > In the area, you can visit Historical Society of Kent County Maryland, Rolphs Wharf Marina, and The Mainstay, then find a cozy spot for a nightcap. Other places to see include Chesapeake Bay and Garfield Center for the Arts at the Prince Theater. ### When is the best time to visit Chestertown? > Visiting local bars in Chestertown is better when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches. ### How can I get to Chestertown and around the area? > You might want to make the most of these transportation options in and around Chestertown: Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. 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