Title: Chestertown Guest Houses from CA $156 | 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 Guest Houses in Chestertown from CA $156 ![](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chestertown Guest Houses ![Bar (on property)](https://images.trvl-media.com/lodging/75000000/74820000/74816700/74816628/19cd2c45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/75000000/74820000/74816700/74816628/b2670143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/75000000/74820000/74816700/74816628/24b9d3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/75000000/74820000/74816700/74816628/b7e89fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn of Lake George Lake George 9.6/10 Exceptional (101) "Beautiful and well kept inn, we had a great stay and vacation for 4th of July weekend! " CA $141 CA $156 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lake-George-Hotels-The-Inn-Of-Lake-George.h74816628.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=2025-10-28&endDate=2025-10-29®ionId=89045&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d89045-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Guest-Houses.d89045-aaGuestHouses.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Baymont by Wyndham Queensbury / Lake George](//images.trvl-media.com/lodging/1000000/30000/23700/23630/cf943129_y.jpg) ### Baymont by Wyndham Queensbury / Lake George 10/10 Excellent "Clean room Very pleasant stsy" [](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.Hotel-Information) ![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](//images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/b0a450bb_y.jpg) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY 10/10 Excellent "Great" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Lakefront Terrace Resort](//images.trvl-media.com/lodging/1000000/900000/899000/898952/7471e44f_y.jpg) ### Lakefront Terrace Resort 10/10 Excellent "all good super friendly staff. good location." [](https://expedia.ca/Lake-George-Hotels-Lakefront-Terrace-Resort.h898952.Hotel-Information) ![Admiral Motel](//images.trvl-media.com/lodging/19000000/18530000/18528500/18528423/a3b9e25a_y.jpg) ### Admiral Motel 10/10 Excellent "Great host and staff. Reasonably priced." [](https://expedia.ca/Lake-George-Hotels-Admiral-Motel.h18528423.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lake George](//images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/4b0bd02a_y.jpg) ### La Quinta Inn & Suites by Wyndham Lake George 10/10 Excellent "Front desk Staff was very pleasant given the amount of people in line checking in due to a hockey tournament in the area" [](https://expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) ![Comfort Inn & Suites Lake George](//images.trvl-media.com/lodging/2000000/1650000/1640200/1640103/93d3500a_y.jpg) ### Comfort Inn & Suites Lake George 10/10 Excellent "Quality of beds were very good" [](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.Hotel-Information) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](//images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Clean, great amenities, softttttt sheets!" [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Fort William Henry Hotel and Conference Center](//images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Excellent hotel. Just stayed too short. " [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Lodge at Schroon Lake](//images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/060fd21f_y.jpg) ### Lodge at Schroon Lake 10/10 Excellent "It was fabulous Very clean and Comfortable Staff very accommodating " [](https://expedia.ca/Schroon-Lake-Hotels-Lodge-At-Schroon-Lake.h92466918.Hotel-Information) ## Find out more about Chestertown ## Chestertown Guest Houses information | Number of reviews | 100 | | --- | --- | | Accommodation | 2 Guest Houses | | Lowest Price | CA $156 | | Highest Price | CA $156 | ## 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) - 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