Title: 2 Stars Hotels in Chestertown, Maryland from CA $90 - Find Cheap Chestertown Hotels With 2 Stars | Expedia.ca [Chestertown Travel Guide](https://expedia.ca/Chestertown.dx7215)[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 # 2 Stars Hotels in Chestertown, Maryland from CA $90 ![](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 2 Star Hotels Tonight [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-09&endDate=2025-10-10&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-10&endDate=2025-10-11&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown 2 Star Hotels ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/7ad7fd33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/5f964900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Baltimore/Glen Burnie Glen Burnie 8.2/10 Very good (1005) "The staff was very nice, the beds were comfortable, the breakfast selections were excellent. " CA $143 CA $163 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/58057ff7.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/19c3b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Hotel & Conference Center Medford 7.8/10 Good (1001) "Great stay" CA $150 CA $176 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/0c88ebfd.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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/8f6f9db7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites Bel Air I-95 Exit 77A Edgewood 7.2/10 Good (1005) "Fine would stay again" CA $87 CA $97 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.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) ![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) ![Business centre](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/7c3be532.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 (1006) "I loved EVERYTHING about this hotel!! We will definitely be back" CA $136 CA $157 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/25ad1d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/05b80e5b.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) ### Hampton Inn & Suites Edgewood/Aberdeen-South Edgewood 9.4/10 Exceptional (1003) "Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon " CA $119 CA $133 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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) ![Lobby lounge](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/d7725583.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 (747) "Great place to stay, better than any of the other hotels in the middle river area." CA $172 CA $198 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.Hotel-Information) ![In-room safe, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/9caa403f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/06910f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/0cbdb0f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/d468abf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Aberdeen Aberdeen 7.0/10 Good (895) "Was a great place to stay for 8 hours" CA $101 CA $113 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Aberdeen-Hotels-Days-Inn-By-Wyndham-Aberdeen.h23024.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/932b25b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/e0847094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/748fa5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One queen bed suite non smoking](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/d9f316c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Baltimore/White Marsh Nottingham 7.8/10 Good (1001) "Really enjoyed my stay, the staff were nice." CA $133 CA $154 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreWhite-Marsh.h57004.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) ![Coffee service](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/43f330d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/ee9bd670.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) ### Americas Best Value Inn Edgewood Edgewood 5.6/10 (988) "I always have a good experience with the staff. The motel might not be the greatest, but the staff is always friendly and accommodating. That's why I keep coming back." CA $80 CA $90 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/cc651796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/068178f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn Grasonville 8.0/10 Very good (1005) "Great spot. " CA $163 CA $181 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/600/507/ef21026e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/600/507/5c9bcbb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/e2e5d244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/250ceaaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Aberdeen by IHG Aberdeen 8.6/10 Excellent (419) "Very clean and wonderful staff " CA $181 CA $203 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Aberdeen-Hotels-Holiday-Inn-Express-Aberdeen.h507.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/9c87ac97.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 (776) "Room was clean, price is very reasonable. " CA $130 CA $146 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1157600/1157600/711b46cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 2 Double Beds, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/2000000/1160000/1157600/1157600/c3a5ca1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/2000000/1160000/1157600/1157600/016a121d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1157600/1157600/f5577f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extended Stay America Suites Baltimore Glen Burnie Glen Burnie 6.4/10 (768) "Overall it was a pretty good place to stay. " CA $120 CA $137 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Baltimore-Hotels-Extended-Stay-America-Suites-Baltimore-Glen-Burnie.h1157600.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown Chestertown 7.2/10 Good (400) "We had a great stay with our two Pups.. The room was very nice and comfortable and very clean." CA $114 CA $126 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ![Free continental breakfast](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/ffece2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/cfe3570f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/8c995ed0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express White Marsh by IHG Nottingham 9.6/10 Exceptional (944) "Staff was very nice and rooms were clean. Breakfast was great too!!" CA $133 CA $154 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/ba82ee09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/3cc8ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/6af27243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Middletown by IHG Middletown 9.2/10 Wonderful (626) "Check in staff was awesome!" CA $145 CA $161 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/a0c80d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Middletown Middletown 9.2/10 Wonderful (291) "One of the best hotels I have ever stayed " CA $147 CA $163 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/da06d995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (826) "Friendly staff, clean room, convenient location. " CA $143 CA $159 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/w1822h1320x8y2-6d9bb9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/38c80911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/87321239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Accessible, Non Smoking (Mobility, Roll-In Shower)](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/7b28496f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area Edgewood 7.2/10 Good (1004) "I found the staff to be very friendly, I believe that it is a family owned / operated establishment and while the inside of the hotel " CA $93 CA $104 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Edgewood-Hotels-Wingate-By-Wyndham-Bel-Air-I-95-Exit-77A.h56432.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/12600/12576/205e986f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed (Smoke Free)](https://images.trvl-media.com/lodging/1000000/20000/12600/12576/01924944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/20000/12600/12576/3052aae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/12600/12576/9325a88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Aberdeen Aberdeen 6.4/10 (1003) "The area of the property was the best part lots of choices going out to eat close by hthe attendant I was nice however we had a issue with multiple flits and gnats I’ve killed so many only for them to be more in its place I couldn’t eat my food because it was so many gnats that crawled on my food were I couldn’t eat it." CA $87 CA $97 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Aberdeen-Hotels-Red-Roof-Inn-Aberdeen.h12576.Hotel-Information) ![](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%2F2Star-Chestertown-Hotels.s20-0-d7215.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Chestertown-Hotels.s20-0-d7215.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Chestertown. ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Historic Inns of Annapolis 58 State Circle, Annapolis, MD CA $146 CA $214 total Nov 2 - Nov 3 includes taxes & fees 8.8/10 Excellent! (1,839 reviews) [](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?impolicy=resizecrop&rw=402&ra=fit) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 4 Philadelphia Ct, Rosedale, MD CA $107 CA $123 total Oct 14 - Oct 15 includes taxes & fees 7/10 Good! (1,002 reviews) [](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](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 2112b Emmorton Park Rd, Edgewood, MD CA $118 CA $132 total Oct 12 - Oct 13 includes taxes & fees 8.2/10 Very Good! (1,008 reviews) [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) Still don't see what you're looking for? [See all properties in Chestertown.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=7215&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=7215&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=7215&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=7215&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=7215&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=7215&star=20&star=20&amenities=WATER_PARK) 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. ## 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=2025-10-24&endDate=2025-10-25&adults=2®ionId=7215) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) Photo by Assya A ## Top Chestertown Hotel Reviews ![Red Roof Inn & Suites Chestertown](//images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg) ### Red Roof Inn & Suites Chestertown 10/10 Excellent "Room temperature was good. Room was also very spacious and clean. " [](https://expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ## Find out more about Chestertown Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Chestertown, Chestertown you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions. Several of the best hotels with 2 Stars in Chestertown are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. 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