Title: Chestertown Guest Houses | 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 ![](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![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) ![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) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/75000000/74820000/74816700/74816628/37b5e126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn of Lake George [](https://www.expedia.ca/Lake-George-Hotels-The-Inn-Of-Lake-George.h74816628.Hotel-Information) Lake George 9.6/10 Exceptional (106 reviews) "Clean room, easy temp control, good fridge and tv. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel [](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=2026-02-08&endDate=2026-02-09®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 ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Room was clean with great views of the park. Staff was fantastic (thanks Tabitha!), and the food was incredible. When the breakfast is that good, you know the dinner will be even better." [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Wonder stay. Very clean and comfortable with friendly staff - housekeeper was excellent!!! The restaurant adjacent was great as well, free breakfast for kids under 11, great omelet station! Will definitely go back !!!" [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![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 "Staff. The lady at the front desk was awesome. We didn’t have a remote in the room and she had one up there in minutes. While there we mentioned a cup and some crumbs under the bureau and she cleaned up herself with a smile. Great job. " [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.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 "Had a great stay. Staff was very friendly and always making sure we had what we needed. " [](https://expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.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 "Yes room r spotless and clean" [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!](https://images.trvl-media.com/lodging/19000000/18040000/18035100/18035092/698e522c_y.jpg) ### HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles! 10/10 Excellent "We loved our visit here. John and Yvonne were wonderful. The space was clean, quiet, and truly magical. The views were second to none and the castle and other buildings are truly worth experiencing. We loved learning about the history of this place and we will certainly be back." [](https://expedia.ca/Lake-George-Hotels-Highlands-Castle.h18035092.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 "Staff was attentive!" [](https://expedia.ca/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.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 "Clean room and fab staff." [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![Home2 Suites by Hilton Queensbury Lake George](https://images.trvl-media.com/lodging/24000000/23380000/23379400/23379339/aecf7228_y.jpg) ### Home2 Suites by Hilton Queensbury Lake George 10/10 Excellent "We arrived half an hour early before the check in and our room was ready. Staff was really friendly. Wide variety of selections for break fast, the lady who is in charge was very sweet and attentive." [](https://expedia.ca/Lake-George-Hotels-Home2-Suites-By-Hilton-Queensbury-Lake-George.h23379339.Hotel-Information) ## Find out more about Chestertown ## Chestertown Guest Houses information | Number of reviews | 106 | | ----------------- | -------------- | | Accommodation | 2 Guest Houses | | Lowest Price | | | Highest Price | | ## 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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