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 # Search Guest Houses in Chestertown - ![](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 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## 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) ![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) ![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) ### The Inn of Lake George Lake George 9.6/10 Exceptional (105) "We had a great time at the Inn. The owner was super friendly and even left us a baby champagne bottle as it was our wedding anniversary! It was easy to check in and check out and the bar area downstairs is amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sanjit [](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=2025-12-23&endDate=2025-12-24®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 ![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 "Everything was great" [](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 "Room for as ready early after long trip and staff person was very nice when we got here !" [](https://expedia.ca/Lake-George-Hotels-Home2-Suites-By-Hilton-Queensbury-Lake-George.h23379339.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 "Love the North Country. Nice hotel thats been around for a piece" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.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 "Everything was perfect, kids enjoyed the whole experience with Santa & his friends, waterpark and also the room. Everything was spotless. Definitely going back! " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.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 "The breakfast staff were incredibly welcoming and attentive, making our morning meal feel like a warm, personalized treat! " [](https://expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Outstanding in every way…highly recommend " [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Lodge at Schroon Lake](https://images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/060fd21f_y.jpg) ### Lodge at Schroon Lake 10/10 Excellent "Nice restaurant- welcoming staff, good live music! " [](https://expedia.ca/Schroon-Lake-Hotels-Lodge-At-Schroon-Lake.h92466918.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 "Very accommodating and friendly staff" [](https://expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![Fort William Henry Hotel and Conference Center](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Friendly staff, wonderful food, beautiful lake views, nice amenities. " [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ## Find out more about Chestertown ## Chestertown Guest Houses information | Number of reviews | 105 | | ----------------- | -------------- | | 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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