Title: Chestertown Condo Rentals from CA $1,003 | 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 $1,003 - ![](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 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) 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 one month [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-06&endDate=2026-02-08&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) ## 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) ### Luxe Row Home Steps to USNA Gate 3! [](https://www.expedia.ca/Annapolis-Hotels-Luxe-Row-Home-Steps-To-USNA-Gate-3.h124410574.Hotel-Information) Historic District CA $211 CA $743 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) ![Exterior](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/4d32484b.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) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/7d0396b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Row Home in Downtown Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.Hotel-Information) Historic District CA $211 CA $1,003 total includes taxes & fees Jan 11 - Jan 12 [](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) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121220000/121219300/121219292/ff822c4f.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) ### Luxury Baltimore Escape [](https://www.expedia.ca/Baltimore-Hotels-Luxury-Baltimore-Escape.h121219292.Hotel-Information) Canton 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 $684 CA $1,203 total includes taxes & fees Jan 10 - Jan 11 [](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) ![Interior](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/5db5573a.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) ![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) ### Two Historic Rowhomes in Downtown Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Two-Historic-Rowhomes-In-Downtown-Annapolis.h124410604.Hotel-Information) Historic District CA $388 CA $1,290 total includes taxes & fees Jan 11 - Jan 12 [](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=2026-01-22&endDate=2026-01-23®ionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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 ## Find out more about Chestertown ## Chestertown Condo Rentals information | Number of reviews | | | ----------------- | --------------- | | Accommodation | 4 Condo Rentals | | Lowest Price | CA $1,003 | | Highest Price | CA $1,203 | ## 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 - 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