Title: Chestertown Castles from CA $1,928 | 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) ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller # Search Castles in Chestertown from CA $1,928 - ![](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 [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chestertown Castles ![Exterior](https://images.trvl-media.com/lodging/19000000/18040000/18035100/18035092/eaa3d336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/19000000/18040000/18035100/18035092/82c314a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18040000/18035100/18035092/698e522c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18040000/18035100/18035092/96b7e169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles! Bolton Landing 9.8/10 Exceptional (16) "Amazing castle! Beautiful views of Lake George. Your own private hidden getaway. The most unique experience in Lake George." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon CA $1,366 CA $1,928 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Lake-George-Hotels-Highlands-Castle.h18035092.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90770000/90766600/90766581/b67d6404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90770000/90766600/90766581/7ac96152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90770000/90766600/90766581/5150fd5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90770000/90766600/90766581/2a81fe26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'The King's Suite' in Highlands Castle Bolton CA $1,504 CA $2,337 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Bolton-Landing-Hotels-The-Kings-Suite-In-Highlands-Castle.h90766581.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90930000/90927100/90927082/81c264c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/91000000/90930000/90927100/90927082/w1008h683x0y0-78472b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90930000/90927100/90927082/a83fcad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90930000/90927100/90927082/19ca4daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'The Royal Bedroom' in Highlands Castle Bolton CA $1,501 CA $2,333 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Bolton-Landing-Hotels-The-Royal-Bedroom-In-Highlands-Castle.h90927082.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=2025-12-16&endDate=2025-12-17®ionId=89045&adults=2&lodging=CASTLE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_89045) ![](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-Castles.d89045-aaCastles.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Castles.d89045-aaCastles.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/b0a450bb_y.jpg) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY 10/10 Excellent "Quiet, clean, comfortable, excellent staff." [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Best Western of Lake George](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/e1f93c73_y.jpg) ### Best Western of Lake George 10/10 Excellent "Very nice gentleman " [](https://expedia.ca/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.Hotel-Information) ![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg) ### Six Flags Great Escape Lodge & Indoor Waterpark 10/10 Excellent "Staff are super friendly, and there are many things to do at the hotel to have fun." [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Wonderful hotel, with lots of old charm!" [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Courtyard by Marriott Lake George](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569_y.jpg) ### Courtyard by Marriott Lake George 10/10 Excellent "Beautiful property close to everything. I booked the room with the balcony and it was just like the pictures. We had dinner at restaurant in the hotel, the food was delicious and great service. Room was very clean and comfortable. We are looking forward to returning in the Spring. " [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lake George](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/4b0bd02a_y.jpg) ### La Quinta Inn & Suites by Wyndham Lake George 10/10 Excellent "Clean & modern rooms and courteous staff" [](https://expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) ![Lodges At Cresthaven](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/4993b753_y.jpg) ### Lodges At Cresthaven 10/10 Excellent "Great !" [](https://expedia.ca/Lake-George-Hotels-Lodges-At-Cresthaven.h1320727.Hotel-Information) ![Hampton Inn & Suites Lake George](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/201ef456_y.jpg) ### Hampton Inn & Suites Lake George 10/10 Excellent "Fantastic breakfast and very accommodating staff. Very clean and cozy " [](https://expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![Super 8 by Wyndham Lake George/Warrensburg Area](https://images.trvl-media.com/lodging/1000000/460000/459800/459792/a069ae03_y.jpg) ### Super 8 by Wyndham Lake George/Warrensburg Area 10/10 Excellent "Staff was super friendly, even remembering us (or more likely our dog!). Room was very clean, bathroom looked like it had been recently updated. (Previous stays had very tired looking bathroom.) Coffee and breakfast bar was actually ready at 6, unlike at other hotels. Coffee was rather good! And actual Half n Half pods were available. Oh, and bonus: they now provide poop bags for picking up after your fur baby. Nice touch! If you go, ask for Rebel, behind the desk. A happy, sweet capuccino colored pitty who wobbles but doesn't fall down (usually), due to a neurological condition. He's a great welcoming comittee of one!" [](https://expedia.ca/Lake-George-Hotels-Super-8-By-Wyndham-Lake-GeorgeWarrensburg-Area.h459792.Hotel-Information) ## Find out more about Chestertown ## Chestertown Castles information | Number of reviews | 15 | | --- | --- | | Accommodation | 6 Castles | | Lowest Price | CA $1,928 | | Highest Price | CA $2,337 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [B&B in Adirondack](https://www.expedia.ca/Adirondack-Bed-And-Breakfast.d6349269-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Adirondack](https://www.expedia.ca/Adirondack-Cabins.d6349269-aaCabins.Travel-Guide-Accommodation) - [Castles in Adirondack](https://www.expedia.ca/Adirondack-Castles.d6349269-aaCastles.Travel-Guide-Accommodation) - [Chalets in Adirondack](https://www.expedia.ca/Adirondack-Chalets.d6349269-aaChalets.Travel-Guide-Accommodation) - [Holiday Park Resorts in Adirondack](https://www.expedia.ca/Adirondack-Holiday-Parks.d6349269-aaHolidayParks.Travel-Guide-Accommodation) - 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