Title: Book the Best BUSINESS Hotels in Chestertown in 2026 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Business Hotels in Chestertown, MD from CA $103 - ![](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 Business Hotels Tonight [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) Tomorrow [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) ## Our top choices for Chestertown business-friendly hotels ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.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/2000000/1710000/1700800/1700736/959c2292.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (861) "Everything was well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ahmed CA $138 CA $153 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/7daf57ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/86edcd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/bcb2d6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/e5cd056f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Edgewood Aberdeen [](https://www.expedia.ca/TownePlace-Suites-Edgewood-Aberdeen.h74651432.Hotel-Information) Aberdeen 9.0/10 Wonderful (96) "Spotless, very good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Efrain CA $149 CA $167 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/TownePlace-Suites-Edgewood-Aberdeen.h74651432.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/48ed0abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/7074520f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/w3837h2556x3y3-eb803e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/ae4c61bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Baltimore / Aberdeen, MD [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) Aberdeen 8.8/10 Excellent (339) "Clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $98 CA $109 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/817be2e3.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/2000000/1790000/1781300/1781239/b90292fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/8628f41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/88cc2eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Smyrna [](https://www.expedia.ca/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information) Smyrna 7.6/10 Good (1002) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $93 CA $103 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Dover-Hotels-Quality-Inn.h1781239.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/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (939) "It was very comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $108 CA $120 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/951120d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/d2d73c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/04e5ff1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/ca1fc66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Aberdeen-Bel Air by IHG [](https://www.expedia.ca/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information) Bel Air 8.0/10 Very good (472) "Good room and service " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $113 CA $127 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.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) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/b2e70f95.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) ![Premium bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/6d549ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Baltimore/Aberdeen [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) Aberdeen 9.0/10 Wonderful (606) "very pet friendly!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) larry CA $134 CA $150 total includes taxes & fees Jan 17 - Jan 18, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/e8c3ab14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/feb5f933.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) ### Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD [](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information) Bel Air 8.8/10 Excellent (1000) "We found the overall hotel and surrounding area very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquelyn CA $108 CA $121 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.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) ![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/05b80e5b.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) ![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 [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) Edgewood 9.2/10 Wonderful (1003) "Room was great staff friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $114 CA $128 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a5912d87.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 [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) Aberdeen 9.0/10 Wonderful (1001) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $122 CA $137 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-10&endDate=2026-01-11®ionId=7215&adults=2&travelerType=business_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "The chef was amazing" [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Best place to stay is the main building" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 10/10 Excellent "Muy buenos " [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Lovely hotel, my favorite place to stay in Annapolis!" [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "Very courteous staff. " [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Yes and yes" [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Awesome night attendant checked us in on 12/18 and have a great breakfast in a.m." [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "Room was very nice. Staff is always very nice." [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.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) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 10/10 Excellent "Clean " [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ## Frequently asked questions ### How much do business-friendly hotels in Chestertown cost? ### Are there any family-friendly hotels in Chestertown that are also business friendly? ### Why book your business-friendly hotel in Chestertown with Expedia? ### How can I find cheap business-friendly hotels in Chestertown? ### What is there to do in Chestertown near my business-friendly hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - 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