Title: Chestertown Condo Rentals from CA $299 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d89045.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d89045.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/db61c46cb1c1e36f625f3b3e306714b5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller # Search Condos Rentals in Chestertown from CA $299 - ![](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 [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chestertown Condo Rentals ![A heated pool](https://images.trvl-media.com/lodging/111000000/110190000/110182600/110182589/f7f370d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110190000/110182600/110182589/9ae6f4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110190000/110182600/110182589/e9463d4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/111000000/110190000/110182600/110182589/d0ef3fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom condo with fitness room, WiFi in Wonderful Lake George Lake George 10/10 Exceptional (1) "We had a wonderful two night stay. Enjoyed the Lake and attractions!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tatyana A. CA $202 CA $299 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Lake-George-Hotels-Charming-2-Bedroom-Condo-With-Fitness-Room.h110182589.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280753/866080c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280753/3cdfba64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280753/d13c291c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280753/9e0ca942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ideal location for cold weather adventures! Lake George CA $249 CA $596 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Lake-George-Hotels-Ideal-Location-For-Cold-Weather-Adventures.h122280753.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280755/d2bd9d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280755/03e5cc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280755/6ad42b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280755/978f6487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect home base for cold weather adventures! Lake George CA $262 CA $612 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Lake-George-Hotels-Perfect-Home-Base-For-Cold-Weather-Adventures.h122280755.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=2025-11-29&endDate=2025-11-30®ionId=89045&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.d89045-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Condos.d89045-aaCondos.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ### Lodges At Cresthaven 10/10 Excellent "Yes, everything was great !" [](https://expedia.ca/Lake-George-Hotels-Lodges-At-Cresthaven.h1320727.Hotel-Information) ### Six Flags Great Escape Lodge & Indoor Waterpark 10/10 Excellent "We were a group of 20 and they were able to put all of our rooms near each other. It was greatly appreciated." [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY 10/10 Excellent "Staff was wonderful and room was nice" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ### The Queensbury Hotel 10/10 Excellent "Well maintained, friendly front desk staff" [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ### Admiral Motel 10/10 Excellent "Parking is easy and the Staff are very friendly, great location. My only negative would be that, pool needs a bit of updating." [](https://expedia.ca/Lake-George-Hotels-Admiral-Motel.h18528423.Hotel-Information) ### La Quinta Inn & Suites by Wyndham Lake George 10/10 Excellent "Everything about our stay was great .The room was clean, the service was wonderful.the pool area was amazing for the kids.Breakfast was perfect with plenty options for the little ones.We will definitely stay here again when we're in the Lake George region ." [](https://expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Good amenities, friendly staff, clean room. " [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ### Courtyard by Marriott Lake George 10/10 Excellent "Great place" [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ### Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area 10/10 Excellent "Clean room! Great staff! Excellent stay!" [](https://expedia.ca/Lake-George-Hotels-Fairfield-Inn-Suites-By-Marriott-Queensbury-Glens-FallsLake-George-Area.h38858716.Hotel-Information) ## Find out more about Chestertown ## Chestertown Condo Rentals information | Number of reviews | 1 | | --- | --- | | Accommodation | 12 Condo Rentals | | Lowest Price | CA $299 | | Highest Price | CA $612 | ## Frequently asked questions ### Why book your condo in Chestertown with Expedia? > Reserving a condo in Chestertown is as easy as deciding on your travel dates and picking an option that checks your boxes. In search of something affordable or luxurious, or a stay that also comes with a kitchen and laundry? Use Expedia's search filters to narrow your results even further and find the perfect pad. ### How can I find cheap condos in Chestertown? > With Expedia's handy filter tool, locating cheap condos in Chestertown is easy. To find accommodations that are easy on your bank balance, narrow down your search by budget, amenities and star rating. ### What is there to do in Chestertown near my condo? > If you're eager to explore the best of Chestertown, find your way to [Loon Lake Beach](https://www.expedia.ca/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction). 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