Title: Chestertown Condo Rentals from CA $1,000 | 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) # Search Condos Rentals in Chestertown from CA $1,000 - ![](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 In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown condo rentals ![Property grounds](https://images.trvl-media.com/lodging/125000000/124420000/124410600/124410574/646644d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124420000/124410600/124410574/ced68cc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/125000000/124420000/124410600/124410574/b0db8051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/125000000/124420000/124410600/124410574/9719840b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Historic District [](https://www.expedia.ca/Annapolis-Hotels-Luxe-Row-Home-Steps-To-USNA-Gate-3.h124410574.Hotel-Information) CA $211 CA $741 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Annapolis-Hotels-Luxe-Row-Home-Steps-To-USNA-Gate-3.h124410574.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/c5b533c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/46ad9c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/4d32484b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/bbbfca07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Historic District [](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.Hotel-Information) CA $211 CA $1,000 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121220000/121219300/121219292/f84c50e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/122000000/121220000/121219300/121219292/0e13886e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121220000/121219300/121219292/ed51b587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121220000/121219300/121219292/ff822c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Canton [](https://www.expedia.ca/Baltimore-Hotels-Luxury-Baltimore-Escape.h121219292.Hotel-Information) 8.0/10 Very good (1) "The location was great so close to where we needed to be. Also very close to shops which was helpful. The kitchen was well appointed. The parking situation was a bit odd but we adjusted. Not sure where the third bedroom was located but luckily our guest did not need accommodations. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer R. CA $682 CA $1,199 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Baltimore-Hotels-Luxury-Baltimore-Escape.h121219292.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/12d60997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/de25e343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/6e5470f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/e11dd506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Historic District [](https://www.expedia.ca/Annapolis-Hotels-Two-Historic-Rowhomes-In-Downtown-Annapolis.h124410604.Hotel-Information) CA $387 CA $1,286 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Annapolis-Hotels-Two-Historic-Rowhomes-In-Downtown-Annapolis.h124410604.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=2026-01-21&endDate=2026-01-22®ionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=CABIN) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=VILLA) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=HOUSE_BOAT) Residences [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=RESIDENCE) ![](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 ![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 "Everything at the hotel was excellent. We had a small dog with us and they were very accommodating. And the breakfast over several days was varied and excellent." [](https://expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.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) ![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 "Very welcoming and room very clean." [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.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 "Valet parking was excellent. The men doing it were friendly and professional. The room was just the right temperature. " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg) ### Home2 Suites by Hilton Baltimore/White Marsh 10/10 Excellent "Cleanliness, friendly staff. Spacious room. Great breakfast." [](https://expedia.ca/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.Hotel-Information) ![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 "Room was very clean...staff was nice..." [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.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 "Breakfast could have been better. Would have been nice to have fresher options. The suite was great, except one remote wasn’t working." [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.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 "Everything was wonderful at this hotel except the breakfast. " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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 "Check in was smooth, room was spacious and clean, free parking and breakfast included. The location near the highway was good for us no waist time for driving travellers " [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ## Find out more about Chestertown ## Chestertown Condo Rentals information | Number of reviews | | | ----------------- | --------------- | | Accommodation | 4 Condo Rentals | | Lowest Price | CA $1,000 | | Highest Price | CA $1,199 | ## Frequently asked questions ### Why book your condo in Chestertown with Expedia? ### How can I find cheap condos in Chestertown? ### What is there to do in Chestertown near my condo? ## 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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