Title: Chestertown Motel: Browse Cheap Motels in Chestertown 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) ![Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr ![](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 prices for these dates Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown motels ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/4510147f.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/b2f6e2fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/056aa897.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/1000000/30000/23100/23024/75cb50a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Aberdeen [](https://www.expedia.ca/Aberdeen-Hotels-Days-Inn-By-Wyndham-Aberdeen.h23024.Hotel-Information) Aberdeen 7.0/10 Good (926 reviews) "Clean rooms, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $81 CA $91 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Aberdeen-Hotels-Days-Inn-By-Wyndham-Aberdeen.h23024.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/5177cf8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/03a31915.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 [](https://www.expedia.ca/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.Hotel-Information) Aberdeen 7.0/10 Good (862 reviews) "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 $76 CA $85 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.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) ![Combined shower/tub, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/304c53d2.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) ### Super 8 by Wyndham Baltimore/Essex Area [](https://www.expedia.ca/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.Hotel-Information) Essex 5.6/10 (418 reviews) "Good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carlos CA $90 CA $104 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.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=2026-01-25&endDate=2026-01-29®ionId=7215&adults=2&lodging=MOTEL&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-Motels.d7215-aaMotels.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Motels.d7215-aaMotels.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![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 "Newer looking hotel. Very nice lobby. Kind of upscale. I’ll stay here again if we come this way." [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Room was clean and comfortable. Staff was courteous " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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 "Kind staff, clean room, and nice accommodations!" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19_y.jpg) ### Fairfield Inn & Suites by Marriott Middletown 10/10 Excellent "This property was amazing. Everything you can ask for in a hotel. The staff is very friendly and always willing to help. The room was very clean. The room and hallway had a very fresh smell. " [](https://expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg) ### Holiday Inn Express White Marsh by IHG 10/10 Excellent "Yes breakfast was fresh but I would prefer real eggs. I don’t like those eggs. Other than that it was good. Parking is great. You might want to get more lighting on the side of the building. Other than that I LOVE my stay at Holiday Inn Express. " [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.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 "Everything was clea" [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.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 "Spotless hotel, staff was beyond incredible. They have won a customer for llife" [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.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 "Delicious breakfast and very spacious rooms. " [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "The hotel was beautiful, and the staff was courteous and friendly. " [](https://expedia.ca/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) ## Find out more about Chestertown ## Chestertown Motels information | Number of reviews | 2,204 | | ----------------- | --------- | | Accommodation | 12 Motels | | Lowest Price | CA $85 | | Highest Price | CA $104 | ## Frequently asked questions ### What can I expect from a motel trip to Chestertown? ### What's it like to stay in a motel? ### What are the best motels in Chestertown? ### What can I do in Chestertown? ### What's the seasonal weather like in Chestertown? ### What are my options for getting around Chestertown when staying in a motel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Best Western Hotels in Aberdeen Proving Ground ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels-Best-Western.0-0-d553248634999428212--bBestWestern.Travel-Guide-Filter-Hotels) - [Aberdeen Proving Ground Hotels ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels.d553248634999428212.Travel-Guide-Hotels) - 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