Title: Chestertown Condo Rentals | 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) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Search Condos Rentals in Chestertown ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chestertown Condo Rentals ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119330000/119327700/119327681/6cf2c348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119327700/119327681/0ab02fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119330000/119327700/119327681/17fb0bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119327700/119327681/f2aff50d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront condo. Completely renovated. Walk to Kent Island's best places Chester [](https://www.expedia.ca/Chester-Hotels-Waterfront-Condo-Completely-Renovated-Walk-To-Kent-Islands-Best-Places.h119327681.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32410000/32401200/32401110/a6910ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32410000/32401200/32401110/904b1187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32410000/32401200/32401110/8f771580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, stereo](https://images.trvl-media.com/lodging/33000000/32410000/32401200/32401110/1d4c3b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Condominium in the heart of the historic center Historic District 9.8/10 Exceptional (284) "The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. " [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Condominium-In-The-Heart-Of-The-Historic-Center.h32401110.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/8ef85715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/7203703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/w906h683x59y0-0dacccf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/c9b4e203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Waterfront Cottage Stevensville 8.8/10 Excellent (11) "Enjoyed fishing at the pier and sitting on the porch" [](https://www.expedia.ca/Stevensville-Hotels-Chester-River-Waterfront-Cottage.h83759327.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/77000000/76460000/76456300/76456299/ebf04a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76460000/76456300/76456299/w1080h720x100y0-e0ef267a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76460000/76456300/76456299/91ffdd22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76460000/76456300/76456299/776a615f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BEACH WITHOUT THE BUSTLE Betterton Beach 10/10 Exceptional (36) "The condo is very nice, nice. Everything we needed. Hoping for another stay in the near future." [](https://www.expedia.ca/Betterton-Hotels-BEACH-WITHOUT-THE-BUSTLE.h76456299.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=2025-10-08&endDate=2025-10-09®ionId=7215&adults=2&lodging=CONDO&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-Condos.d7215-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Condos.d7215-aaCondos.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![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 " Very nice" [](https://expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.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 "Loved our stay! Will visit again soon!!! " [](https://expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) ![SpringHill Suites Baltimore White Marsh/Middle River](//images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/ac399738_y.jpg) ### SpringHill Suites Baltimore White Marsh/Middle River 10/10 Excellent "Only complaint we have is the sofa was very uncomfortable. We used the hotel as home base for 5 days and nights and spent a considerable amount of time in the hotel relaxing and watching tv" [](https://expedia.ca/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.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 10/10 Excellent "The staff were professional and friendly. " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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 10/10 Excellent "Great hotel, room very clean. The man that checked us in was so friendly and informative. " [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Comfort Inn & Suites Chestertown](//images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Great property" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](//images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Clean and quiet " [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ![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 "Nice & friendly staff You’re doing a good job & keep up the good work " [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Stayed for one night; room was nice, easy to access, and located near numerous local attractions. " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ## Find out more about Chestertown ## Chestertown Condo Rentals information | Number of reviews | 291 | | --- | --- | | Accommodation | 5 Condo Rentals | | Lowest Price | | | Highest Price | | ## 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) - [Apartments in Betterton](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - [Hotels near Betterton Beach](https://www.expedia.ca/Betterton-Beach-Hotels.0-l553248635983992889-0.Travel-Guide-Filter-Hotels) - [Cottages in Betterton](https://www.expedia.ca/Betterton-Cottages.d3000440429-aaCottages.Travel-Guide-Accommodation) - 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