Title: Book The Best Hotels in Chestertown, MD for 2025 from CA $91 - Competitive Prices - Expedia.ca [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) ![Eastern Shore small towns in Maryland, USA. Traveling the Eastern Shore points o f Maryland this weekend, we came across this local church with gravestones. We found several of these local churches along with the many farms and inlets leading to the Chesapeake bay.](https://images.trvl-media.com/place/7215/39d32fed-717d-4f49-ae4c-a7eb875f5cb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr # Find hotels in Chestertown, MD from CA $91 ![](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 ## Go beyond your typical stay in Chestertown Ocean view [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=OCEAN_VIEW) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=PETS) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&lodging=COTTAGE) Pool [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=POOL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=HOT_TUB) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&travelerType=family_friendly) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&lodging=APARTMENT) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=WATER_PARK) ## Check prices for these dates Tonight [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 1,074 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/9a7a154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (835) "The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlie CA $143 CA $158 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/8b9992bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown Chestertown 7.2/10 Good (409) "We had a great stay with our two Pups.. The room was very nice and comfortable and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $113 CA $126 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.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) ![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) ### 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 $185 CA $212 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/bb9281c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/dfe0704f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/b1fff75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh Rosedale 7.0/10 Good (1035) "Had a nice stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy CA $100 CA $115 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.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 (908) "Nice Holiday Inn Express with great water views." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $155 CA $172 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Desk, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/ff324f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/29162b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/abecbdac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites Bel Air I-95 Exit 77A Edgewood 7.4/10 Good (1005) "Nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick CA $88 CA $99 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite (2 Queen Beds with Sofa bed)](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/65534781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/19c3b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/a9a9ef59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Hotel & Conference Center Medford 7.8/10 Good (1000) "Stayed here and went to Lil Duval show, very nice place...would absolutely stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacey CA $149 CA $175 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/0c8b9f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/12e4e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/114f1de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Baltimore North, MD Rossville 7.2/10 Good (1004) "I have been staying here for some time now and I've always been happy and every time I come in they always remember me very welcoming very helpful above and beyond service and always ask how the families doing how I'm doing it's like being home when you're away from home very happy with the place very clean rooms very nice affordable prices and staff does an amazing job working hard on keeping the place clean amazing breakfast rooms are always clean the whole place and the staff and give it a 10... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $133 CA $154 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/9f4cdea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/c6592633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/4e480368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Aberdeen near APG Aberdeen 7.8/10 Good (790) "The front desk staff were friendly and welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bonnie CA $124 CA $138 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two queen studio suite](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/4152f194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/25ad1d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/19cae57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Edgewood/Aberdeen-South Edgewood 9.4/10 Exceptional (1005) "Would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dena CA $117 CA $131 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/7c3be532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/ad2aa516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/0dd46a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott White Marsh Nottingham 8.6/10 Excellent (1010) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teresa CA $132 CA $152 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/1c55f3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/c1cd1534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/43f330d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Americas Best Value Inn Edgewood Edgewood 5.6/10 (998) "Stayed 3 nights. The beds were comfortable, the rooms were clean. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Michelle CA $84 CA $94 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.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) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.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) ### Hyatt Place Kent Narrows & Marina Grasonville 9.4/10 Exceptional (642) "Nice location and restaurants galore in area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $208 CA $231 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort Stevensville 9.2/10 Wonderful (121) "Great INN super nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $220 CA $295 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/dd2808c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/2b727b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/61b9d981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/0707a932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Baltimore/Essex Area Essex 5.4/10 (401) "Just a nice quiet cool place clean rooms and the bed is away from the door lol" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamelle CA $117 CA $136 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/47756559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/0ab02da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/8dff74ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/b2e70f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Baltimore/Aberdeen Aberdeen 9.0/10 Wonderful (588) "Wonderful room and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caren CA $135 CA $151 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/180b8972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking (One-Bedroom)](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/fb66f5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/e64b8ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/a1cb4d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Aberdeen MD Aberdeen 7.0/10 Good (853) "Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelly CA $81 CA $91 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/6a2a39d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/30dd6273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/07e31512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Baltimore Bayview Campus Hopkins Bayview 9.0/10 Wonderful (1004) "We’ve stayed here two times already and always enjoyed it! Clean rooms, friendly staff, free parking and many shopping options close by!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander CA $167 CA $197 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.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/c1b842f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1866) "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 CA $145 CA $213 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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/2000000/1230000/1222200/1222176/66a1e121.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/d03cf3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina Grasonville 9.0/10 Wonderful (1000) "Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta CA $194 CA $215 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.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=2025-11-11&endDate=2025-11-12®ionId=7215&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels) ## Learn more about Chestertown Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour. [See all hotels in Chestertown](https://www.expedia.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12&adults=2®ionId=7215) ![Eastern Shore small towns in Maryland, USA. Traveling the Eastern Shore points o f Maryland this weekend, we came across this local church with gravestones. We found several of these local churches along with the many farms and inlets leading to the Chesapeake bay.](https://images.trvl-media.com/place/7215/39d32fed-717d-4f49-ae4c-a7eb875f5cb2.jpg?impolicy=fcrop&w=730&h=1102&p=1&q=high) Photo by Patricia Knorr ### Stay near popular Chestertown attractions [](https://expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) #### Washington College Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000403) [](https://expedia.ca/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels) #### Rolphs Wharf Marina Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561879605) [](https://expedia.ca/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) #### River Arts Chestertown Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662298) [](https://expedia.ca/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels) #### Historical Society of Kent County Maryland You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000400) [](https://expedia.ca/Wilmer-Park-Hotels.0-l553248621561000402-0.Travel-Guide-Filter-Hotels) #### Wilmer Park Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000402) [](https://expedia.ca/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) #### Garfield Center for the Arts at the Prince Theater You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000401) ## More cheap stays in Chestertown ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn & Suites Bel Air I-95 Exit 77A 2112a Emmorton Park Road, Edgewood, MD CA $88 CA $99 total Oct 29 - Oct 30 includes taxes & fees 7.2/10 Good! (1,005 reviews) [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Holiday Inn Express White Marsh by IHG 10542 Philadelphia Road, White Marsh, MD CA $134 CA $155 total Nov 24 - Nov 25 includes taxes & fees 9.4/10 Exceptional! (960 reviews) [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Americas Best Value Inn Edgewood 1709 Edgewood Road, Edgewood, MD CA $84 CA $94 total Oct 29 - Oct 30 includes taxes & fees 5.6/10 (997 reviews) [](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Fairfield Inn & Suites by Marriott White Marsh 8477 Cordon Way, Baltimore, MD CA $132 CA $152 total Nov 23 - Nov 24 includes taxes & fees 8.4/10 Very Good! (1,009 reviews) [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Days Inn by Wyndham Aberdeen](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/9caa403f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Days Inn by Wyndham Aberdeen 783 W Bel Air Ave, Aberdeen, MD CA $93 CA $104 total Nov 2 - Nov 3 includes taxes & fees 7/10 Good! (899 reviews) [](https://expedia.ca/Aberdeen-Hotels-Days-Inn-By-Wyndham-Aberdeen.h23024.Hotel-Information) ![Comfort Inn & Suites Aberdeen near APG](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Aberdeen near APG 980 Hospitality Way, Aberdeen, MD CA $124 CA $138 total Nov 2 - Nov 3 includes taxes & fees 7.8/10 Good! (790 reviews) [](https://expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) ## Hotels in Chestertown with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_w.jpg) 5 Star Hotels 1 properties [](https://expedia.ca/5Star-Chestertown-Hotels.s50-0-d7215.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_w.jpg) 4 Star Hotels 2 properties [](https://expedia.ca/4Star-Chestertown-Hotels.s40-0-d7215.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_w.jpg) 3 Star Hotels 74 properties [](https://expedia.ca/3Star-Chestertown-Hotels.s30-0-d7215.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_w.jpg) 2 Star Hotels 165 properties [](https://expedia.ca/2Star-Chestertown-Hotels.s20-0-d7215.Travel-Guide-Filter-Hotels) ## Find out more about Chestertown ### Top reasons to visit Chestertown - **Scenic Outdoor Adventures:** Experience beautiful landscapes and recreational activities along the picturesque Chester River. - **Charming Downtown:** Stroll along Main Street to discover delightful shops and local attractions. - **Rich Historical Experience:** Explore the town's rich heritage through house tours and historic sites. - **Festive Community Events:** Enjoy lively holiday activities and festivals that showcase the warmth of the community. - **Diverse Accommodation Options:** Find a range of pet-friendly and welcoming stays for all types of travellers. ### Find great hotels near Chestertown Explore a variety of accommodation options in Chestertown, Maryland, where you can find pet-friendly hotels and motels, perfect for business travellers and those seeking an LGBTQIA welcoming environment. Whether you're looking for vacation rentals, suites, or house rentals, Chestertown offers a range of choices to ensure a comfortable and enjoyable stay in this charming riverside town. - **[Quality Inn & Suites Bel Air I-95 Exit 77A:](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)** A prime choice for business travellers, Quality Inn & Suites Bel Air I-95 Exit 77A combines convenience and professionalism. Located 33.8km from Chestertown, this hotel offers an array of amenities designed to cater to business needs, such as meeting rooms, free Wi-Fi, and a business centre. Guests have praised the comfortable rooms, ideal for unwinding after a busy day of meetings, along with complimentary breakfast options to kickstart their mornings. Its strategic location near major highways makes it an excellent stop for those on the go. - **[La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A:](https://www.expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information)** This welcoming hotel, situated 33.8km from Chestertown, is a haven for pet owners and travellers seeking relaxation. La Quinta Inn & Suites features a pet-friendly policy, allowing dogs and cats to stay with their owners, making it perfect for those travelling with furry friends. Guests appreciate the spacious rooms and complimentary breakfast, which provides a delightful start to their day. The hotel also boasts a convenient location near local attractions and dining options, ensuring an enjoyable and hassle-free stay for all. - **[Red Roof Inn Aberdeen:](https://www.expedia.ca/Aberdeen-Hotels-Red-Roof-Inn-Aberdeen.h12576.Hotel-Information)** Located 35.4km from Chestertown, Red Roof Inn Aberdeen is a vibrant option for pet-lovers and LGBTQIA-friendly travellers. This hotel not only welcomes pets but also supports an inclusive environment, making it a comfortable choice for all guests. With amenities that allow pets in rooms and a waived fee for service animals, it’s designed with comfort in mind. Guests have highlighted the affordable rates, clean accommodations, and friendly staff, making it a popular choice for those looking for a welcoming getaway. ### Where to stay in and around Chestertown Chestertown, Maryland, offers a delightful blend of outdoor adventures and rich history, perfect for a family-friendly getaway. Explore charming neighbourhoods and discover friendly resorts that capture the essence of hometown holidays. Enjoy the scenic beauty while soaking in the historical atmosphere, making it an ideal destination for a relaxing weekend escape. Experience the warmth of the community during the holiday season and uncover the hidden gems that make Chestertown a must-visit spot. - **[Worton:](https://www.expedia.ca/Worton-Hotels.d3000440948.Travel-Guide-Hotels)** Located a mere 6.4km from Chestertown, Worton offers a charming escape for those seeking outdoor adventures and stunning scenery. While the number of visitors fluctuates throughout the year, the peak seasons in April to May and July draw in nature enthusiasts eager to explore its recreational areas and nearby national parks. With attractions such as beautiful beaches and marinas, Worton is perfect for a leisurely day of exploration or fun-filled activities on the water. - **[Georgetown:](https://www.expedia.ca/Georgetown-Hotels.d553248635975874069.Travel-Guide-Hotels)** Nestled in the vicinity of Chestertown, Georgetown is a quaint village that captivates visitors with its romantic outdoor settings and adventurous spirit. The peak tourist months from June to August offer a lively atmosphere, where you can engage in various recreational activities or relax at local recreation centres. Notable landmarks like sports facilities and a stadium enhance the area’s appeal, making it an excellent spot for those looking to combine relaxation with a dash of excitement. - **[Tolchester Beach:](https://www.expedia.ca/Tolchester-Beach-Hotels.d553248635975848245.Travel-Guide-Hotels)** As a delightful village close to Chestertown, Tolchester Beach is an ideal destination for beach lovers and those yearning for natural beauty. While it experiences consistent visitor numbers throughout the year, summer months from June to August are particularly popular. Enjoy leisurely strolls along the boardwalk or take advantage of the recreational areas and nearby marinas. With its proximity to national parks and serene beaches, Tolchester Beach promises a refreshing getaway filled with outdoor enjoyment. ### Things to do in and around Chestertown Chestertown, Maryland, is perfect for an outdoor getaway, offering beautiful scenery and a range of activities. Visitors can enjoy house tours, explore recreational areas, stroll along the boardwalk, and participate in festival events. The downtown area hosts festive holiday activities, making it an ideal spot for a weekend escape or day trip, ensuring a delightful experience for all who visit. **Shopping** In Chestertown, you can enjoy local shops and boutiques for unique gifts. If you're up for a drive, visit the [Queenstown Premium Outlets](https://www.expedia.ca/Queenstown-Premium-Outlets-Hotels.0-l553248621532662352-0.Travel-Guide-Filter-Hotels), located 27.4km away, for brand-name bargains. [Paul Reed Smith Guitars](https://www.expedia.ca/Paul-Reed-Smith-Guitars-Hotels.0-l747757786500468736-0.Travel-Guide-Filter-Hotels), 33.8km away, offers a unique shopping experience for music enthusiasts. **Recreation** At [Ripken Stadium](https://www.expedia.ca/Ripken-Stadium-Hotels.0-l6145161-0.Travel-Guide-Filter-Hotels), you can immerse yourself in the vibrant sports atmosphere while enjoying various recreational events. Meanwhile, the [Queenstown Harbor Golf Club](https://www.expedia.ca/Queenstown-Harbor-Golf-Club-Hotels.0-l6091731-0.Travel-Guide-Filter-Hotels) and [Queenstown Harbor Golf Links](https://www.expedia.ca/Queenstown-Harbor-Golf-Links-Hotels.0-l553248621532662350-0.Travel-Guide-Filter-Hotels) offer beautiful outdoor settings for a relaxing yet active day on the greens, surrounded by nature's beauty. **Adventure** At the [Annapolis Sailing School](https://www.expedia.ca/Annapolis-Sailing-School-Hotels.0-l553248621532662324-0.Travel-Guide-Filter-Hotels), located 45.1km from Chestertown, you can immerse yourself in thrilling sailing experiences on the beautiful Chesapeake Bay. Alternatively, the Emmorton Recreation & Tennis Center, 38.6km away, offers various engaging recreational activities, while the Tose Family Tennis Center, also 45.1km away, boasts fantastic tennis facilities. **Nightlife** In Chestertown, the [Garfield Center for the Arts at the Prince Theater](https://www.expedia.ca/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) offers vibrant performances in a charming atmosphere. Just a short drive away, [Church Hill Theatre](https://www.expedia.ca/Church-Hill-Theatre-Hotels.0-l844528418122231808-0.Travel-Guide-Filter-Hotels) and [Avalon Theatre](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) also provide engaging shows, each with a touch of culture and romance, perfect for a delightful evening out. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Booking tips and Expedia advantages for Chestertown For a budget-friendly trip to Chestertown, consider visiting between January to February or November for lower accommodation rates. Tuesdays are the cheapest days to stay, while Saturdays tend to be pricier. Use Expedia’s search tool to find budget options, including eco-friendly hotels, and filter by price to uncover the best deals. Additionally, you can save money by bundling your hotel, flights, and activities into an Expedia package. Don’t forget to explore free local attractions to enhance your experience while keeping costs down. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chestertown are January to February and November, where the prices are slightly lower. This is in comparison to June to July and 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 Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to customize your travel preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save some money by combining your Chestertown hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions in Chestertown Chestertown, Maryland, offers a delightful mix of outdoor adventures and scenic beauty, perfect for a family beach vacation. Visitors can explore urban parks, marinas, and the picturesque Chester River. A stroll down Main Street Chestertown reveals charming shops and local attractions, making it an ideal destination for those seeking a relaxing getaway in nature. - **[Washington College:](https://www.expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels)** Experience the charm of this historic institution, renowned for its picturesque campus and rich cultural heritage. Engage in various events, art exhibitions, and lectures that showcase the vibrant academic community. - **[Rolphs Wharf Marina:](https://www.expedia.ca/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels)** Dive into outdoor adventures at this scenic marina. Enjoy kayaking, paddleboarding, or simply relaxing by the water's edge, surrounded by beautiful beach vibes and stunning views of the Chester River. - **[Historical Society of Kent County Maryland:](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels)** Discover the local history at this engaging museum. Explore fascinating exhibits that highlight the region's past, offering insight into the culture and traditions of Kent County. ### Best time to go to Chestertown The best time to visit Chestertown is dependant 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 | 34.2°F (1.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | March | 43.7°F (6.5°C) | Light Rain | Mostly Sunny | Average | Average | | April | 54.3°F (12.4°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Average | | June | 72.1°F (22.3°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 77.4°F (25.2°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 75.6°F (24.2°C) | Light Rain | Mostly Sunny | Average | Average | | September | 69.4°F (20.8°C) | Light Rain | Mostly Sunny | Average | Average | | October | 59.2°F (15.1°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 47.3°F (8.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | December | 40.1°F (4.5°C) | Light Rain | Mostly Sunny | Slightly Low | Average | ### The nearest major airports for your trip to Chestertown Chestertown, Maryland, can be conveniently accessed via three major airports. Washington, DC ([DCA](https://www.expedia.ca/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels)\-Ronald Reagan Washington National) is located 93.3km away, with notable hotels like the 5-star InterContinental Washington D.C. - The Wharf and [Riggs Washington DC](https://www.expedia.ca/Washington-Hotels-Riggs-Washington-DC.h37192042.Hotel-Information), both within 4.8km. Baltimore, MD ([BWI](https://www.expedia.ca/Baltimore-Washington-Intl-Thurgood-Marshall-Airport-Hotels.0-aBWI-0.Travel-Guide-Filter-Hotels)\-Baltimore Washington Intl. Thurgood Marshall) is closer at 51.5km, featuring luxurious options such as the [Sagamore Pendry Baltimore](https://www.expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) and [Four Seasons Hotel Baltimore](https://www.expedia.ca/Baltimore-Hotels-Four-Seasons-Hotel-Baltimore.h4603198.Hotel-Information), both 12.9km from the airport, offering shuttle services. Lastly, Baltimore, MD ([MTN](https://www.expedia.ca/Martin-State-Airport-Hotels.0-aMTN-0.Travel-Guide-Filter-Hotels)\-Martin State) lies 32.2km away, with hotels like [Canopy by Hilton Baltimore Harbor Point](https://www.expedia.ca/Baltimore-Hotels-Canopy-By-Hilton-Baltimore-Harbor-Point.h45976006.Hotel-Information) and [Hyatt Place Baltimore Inner Harbor](https://www.expedia.ca/Baltimore-Hotels-Hyatt-Place-Baltimore-Inner-Harbor.h8842065.Hotel-Information), both around 16.1km from the airport. ## Recent reviews of Chestertown hotels ![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 5/5 Excellent "I liked the breakfast because it had cold stuff. And good hot food. Eggs Sausage waffles and juice. " A verified traveller stayed at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh Posted 15 hours ago [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](//images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 5/5 Excellent "Clean room and quiet enough to sleep through the afternoon. " A verified traveller from Stewartstown stayed at La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A Posted 15 hours ago [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 5/5 Excellent "Lovely room" A verified traveller stayed at Historic Inns of Annapolis Posted 17 hours ago [](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 5/5 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 " A verified traveller stayed at Best Western Plus Hotel & Conference Center Posted 2 days ago [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Courtyard by Marriott Baltimore Downtown/McHenry Row](//images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798_y.jpg) ### Courtyard by Marriott Baltimore Downtown/McHenry Row 5/5 Excellent "Great location and felt very safe. Very friendly staff and rooms were clean. " A verified traveller stayed at Courtyard by Marriott Baltimore Downtown/McHenry Row Posted 2 days ago [](https://expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](//images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 5/5 Excellent "Great place to stay" A verified traveller stayed at Fairfield Inn & Suites by Marriott White Marsh Posted 2 days ago [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Holiday Inn Express White Marsh by IHG](//images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg) ### Holiday Inn Express White Marsh by IHG 5/5 Excellent "Must be a new property. Clean and immaculate." A verified traveller stayed at Holiday Inn Express White Marsh by IHG Posted 3 days ago [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.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 5/5 Excellent "On arrival we met Catalina on reception. An extremely pleasant and helpful girl. After that our stay was very comfortable." A verified traveller stayed at Hilton Garden Inn Baltimore/White Marsh Posted 4 days ago [](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 5/5 Excellent "Staff" A verified traveller stayed at Americas Best Value Inn Edgewood Posted 6 days ago [](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ## Frequently asked questions ### Which area of Chestertown is best to stay in for luxury hotels? > The best area to stay in Chestertown for luxury hotels is the historic downtown area, particularly along High Street and Water Street. > > > > This core district is the heart of Chestertown, known for its well-preserved 18th-century architecture and tree-lined streets. It's very walkable, with most shops, galleries, and restaurants concentrated within a few blocks of the Chester River waterfront. You'll find landmarks like the Custom House and the Garfield Centre for the Arts here. > > > > Couples looking for a refined getaway will find this area particularly appealing. The historic inns and boutique hotels often feature elegant decor, fine dining options, and views of the river, providing a sophisticated and relaxing experience. Strolling along the waterfront or browsing the independent shops makes for a pleasant day. > > > > For those travelling for business or attending events at Washington College, staying in the historic downtown offers convenience and quality. ### How much does a luxury hotel in Chestertown cost? > Luxury hotel prices in Chestertown vary, but you can find a great deal from CA $91 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates. ### What luxury activities and experiences are there in Chestertown? > The Chestertown area offers several luxury activities and experiences, focusing on fine dining, bespoke shopping, and exclusive water-based recreation. > > > > For those who appreciate exquisite cuisine and a refined atmosphere, consider a private chef experience at your accommodation or dining at one of the upscale restaurants along High Street, known for their locally sourced ingredients and extensive wine lists. Many offer tasting menus that showcase the region's culinary excellence. > > > > Couples looking for a unique and memorable experience might enjoy a private sailing charter on the Chester River. You can arrange for a skippered yacht to explore the waterways, perhaps with a gourmet picnic basket and champagne. This offers a tranquil and exclusive way to see the natural beauty of the Eastern Shore. > > > > Independent travellers might find bespoke shopping experiences appealing, particularly in the boutiques located on and around Cross Street. Here, you can discover handcrafted jewellery, custom-made clothing, and artisanal home goods, often meeting the creators themselves. ### How can I save on a luxury hotel in Chestertown with Expedia? > There are plenty of ways to save on a luxury hotel in Chestertown. Unlock our lowest prices by joining [One Key™](https://www.expedia.ca/welcome-one-key), Expedia's travel rewards program. It's free and easy to sign up, and you can access member perks too. Typically, booking in advance will help you save on your luxury hotel booking. If you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book a luxury Chestertown hotel and flights as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### Can I cancel my luxury hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right luxury hotel in Chestertown for you. ### How can I save on a Chestertown hotel booking with Expedia? > Before booking your Chestertown hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia. ### How much is the nightly rate at a Chestertown hotel? > Prices for hotels in Chestertown often vary, but you can find a great deal from CA $91 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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