Title: 3 Stars Hotels in Chestertown, Maryland from CA $123 - Find Cheap Chestertown Hotels With 3 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 # 3 Stars Hotels in Chestertown, Maryland 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 3 Star Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-12&endDate=2025-10-13&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=30&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=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown 3 Star Hotels ![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 (1847) "The hotel was absolutely clean and close to the shops and restaurants. " CA $145 CA $214 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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) ![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) ![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) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh Rosedale 7.0/10 Good (1019) "Had a nice stay " CA $106 CA $123 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Studio Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/326b1394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/076885b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/43e68970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A Edgewood 8.2/10 Very good (1014) "Our stay was very good enjoyed the continental breakfast and how close the hotel was to other amenities " CA $118 CA $132 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/6e9faa08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/b77a7385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/b385545e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Baltimore/White Marsh Nottingham 7.8/10 Good (1012) "Great stay" CA $134 CA $154 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/9d10475b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a8370cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a7c447e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG Aberdeen 9.0/10 Wonderful (1006) "Loved our stay! Will visit again soon!!! " CA $139 CA $156 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.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/3000000/2410000/2410000/2410000/114f1de7.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/3000000/2410000/2410000/2410000/0c8b9f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Baltimore North, MD Rossville 7.2/10 Good (1006) "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... CA $128 CA $148 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/bd8b7105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/4cc768f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/c35aa4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Baltimore Downtown/McHenry Row Locust Point 9.0/10 Wonderful (674) "Great location " CA $177 CA $208 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.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) ![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) ![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) ### Hampton Inn Baltimore Bayview Campus Hopkins Bayview 9.0/10 Wonderful (1007) "We’ve stayed here two times already and always enjoyed it! Clean rooms, friendly staff, free parking and many shopping options close by!" CA $183 CA $215 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.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 (638) "Great location and rooms. Great place!" CA $202 CA $224 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/1c3a6583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/b5f07127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/e8c3ab14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/96c882ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD Bel Air 8.8/10 Excellent (1004) "We found the overall hotel and surrounding area very nice. " CA $118 CA $132 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/5447d770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/17516077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/0072ddc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Baltimore/White Marsh Nottingham 8.0/10 Very good (1007) "Clean rooms staff very nice " CA $148 CA $171 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.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) ![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/2000000/1230000/1222200/1222176/66a1e121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/e17d8d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina Grasonville 9.0/10 Wonderful (1003) "Hotel was great, beautiful location near the water" CA $206 CA $228 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2.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/1000000/30000/21100/21017/c97041ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/2f8ab1f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/d0b96c98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Garner Hotel Glen Burnie BWI Airport Area by IHG Glen Burnie 6.6/10 (1007) "Very clean and the staff were very friendly!" CA $111 CA $126 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 19.90 per person)](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/b358be96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/e343ffe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/d1715c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Henderson's Wharf, an Ascend Collection Hotel Fells Point 9.2/10 Wonderful (740) "Really lovely stay- clean and very helpful staff! " CA $221 CA $287 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/898500/898446/86a9f017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/900000/898500/898446/e7c2a28a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/900000/898500/898446/840fad18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/900000/898500/898446/aa748a90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Belcamp - Aberdeen Area by IHG Belcamp 8.4/10 Very good (725) "It was a good location. Workers are super friendly and attentive. " CA $122 CA $137 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Belcamp-Hotels-Holiday-Inn-Belcamp-Aberdeen-Area.h898446.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/915700/915682/00231c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LCD TV, pay movies, streaming services](https://images.trvl-media.com/lodging/1000000/920000/915700/915682/8e4e8b24.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/1000000/920000/915700/915682/3d0843c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/915700/915682/9f59a81e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Baltimore White Marsh Nottingham 8.4/10 Very good (550) "I was very pleased with the stay." CA $154 CA $177 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-Residence-Inn-By-Marriott-Baltimore-White-Marsh.h915682.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) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/1f3f9838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/71bdd057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/96859422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Bel Air Bel Air 9.2/10 Wonderful (215) "The staff was amazing" CA $163 CA $183 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/3c250b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/88d1de79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/fafda427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/6380c7ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Aberdeen Aberdeen 8.6/10 Excellent (626) "Close to restaurants, friendly staff, nice room, food was great" CA $150 CA $168 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/95ae72cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/d1bf2404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/5a18ae7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/73223236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Edgewood/Aberdeen Bel Air 8.8/10 Excellent (355) "Location was great and staff very nice" CA $162 CA $182 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Bel-Air-Hotels-SpringHill-Suites-By-Marriott-EdgewoodAberdeen.h696211.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) ![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) ![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) ### The Lodge at Great Oak Landing Chestertown 7.8/10 Good (70) "Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!" CA $185 CA $212 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.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%2F3Star-Chestertown-Hotels.s30-0-d7215.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F3Star-Chestertown-Hotels.s30-0-d7215.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 3-star hotels. See all 4-star hotels in Chestertown. ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Annapolis Waterfront Hotel, Autograph Collection 80 Compromise St, Annapolis, MD CA $285 CA $324 total Nov 9 - Nov 10 includes taxes & fees 8.8/10 Excellent! (870 reviews) [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![The Inn at Chesapeake Bay Beach Club](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Inn at Chesapeake Bay Beach Club 180 Pier One Road, Stevensville, MD CA $271 CA $337 total Nov 9 - Nov 10 includes taxes & fees 9.4/10 Exceptional! (421 reviews) [](https://expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.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=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=7215&star=30) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=7215&star=30&star=30&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=7215&star=30&star=30&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=7215&star=30&star=30&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=7215&star=30&star=30&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=7215&star=30&star=30&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=2025-10-27&endDate=2025-10-28&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 ![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 "Very nice and clean" [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Aberdeen-APG](//images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3_y.jpg) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG 10/10 Excellent "Nice n clean" [](https://expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) ![The Inn at Henderson's Wharf, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff_y.jpg) ### The Inn at Henderson's Wharf, an Ascend Collection Hotel 10/10 Excellent "Beautiful location and a great stay. Eric at the front desk was great!" [](https://expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.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 10/10 Excellent "Great location " [](https://expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.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 "Loved it" [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.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 "everything was very professional." [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](//images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Everything was fantastic." [](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.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 10/10 Excellent "good" [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ## Find out more about Chestertown The top 3 Stars hotels in Chestertown, Chestertown may offer some of the best discounts and rates, but these properties are anything but average. Travelers love Chestertown 3 Stars hotels for their top quality services, just-like-home amenities, and wallet-friendly prices. You can even get access to fantastic perks like delectable restaurants, so-cool cocktail bars, and spacious fitness centres. Use the travel tools at Expedia.ca to find a cheap deal on a 3 Stars upscale hotel in Chestertown for a first-class experience, or book an inexpensive rate on one of the cheap 3 Stars hotels in Chestertown neighbourhoods near the city’s best attractions. We’ll even help you find vacation packages to go with your three star hotel in Chestertown. From last-minute work trips to long-awaited family getaways, we offer all the essentials you need to enjoy your jaunt through Chestertown. ## Frequently asked questions ### How much does it cost to stay in a 3-star hotel in Chestertown? > To score a reasonably priced 3-star hotel in Chestertown, use Expedia's handy filter tool. Decide on your budget, pick your desired amenities and lots more. Additionally, you can arrange your search results so the least expensive options are shown first. > > > > - Search for the lowest price per night right now from CA $324 ### What is the difference between a 4-star and 3-star hotel in Chestertown? > Reserve a room at a 3-star hotel and you can look forward to clean and comfortable rooms and amenities such as complimentary WiFi, gym equipment and coffee and tea making facilities. These properties may also offer a bar and restaurant. Upgrade your Chestertown getaway by locking in a 4-star hotel. With things like a spa, round-the-clock room service and deluxe toiletries, you'll experience a heightened level of relaxation and comfort. ### What is the difference between a 3-star hotel and a motel in Chestertown? > A motel is a good option if you're planning to tour around Chestertown. These getaways are usually located close to airports and highways, feature on-site parking and come with basic amenities and services. Spend your stay at a 3-star hotel and you'll be more centrally located. 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