Title: Chestertown Guest Houses from CA $153 | 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 [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-05-15&endDate=2026-05-17&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) ![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) ![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 (108 reviews) "Clean room, easy temp control, good fridge and tv. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel CA $138 CA $153 total includes taxes & fees Mar 26 - Mar 27 [](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=2026-04-02&endDate=2026-04-03®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 ![La Quinta Inn & Suites by Wyndham Lake George](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/85a37759_y.jpg) ### La Quinta Inn & Suites by Wyndham Lake George 10/10 Excellent "It’s great every time we stay " [](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 2/10 Terrible "Bed bugs Beware !! " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![Comfort Inn & Suites Lake George](https://images.trvl-media.com/lodging/2000000/1650000/1640200/1640103/93d3500a_y.jpg) ### Comfort Inn & Suites Lake George 10/10 Excellent "Very much so" [](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.Hotel-Information) ![Courtyard by Marriott Lake George](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/6dc91933_y.jpg) ### Courtyard by Marriott Lake George 10/10 Excellent "Great visit! " [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/2f07bb66_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Always enjoy our stay here. " [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Fort William Henry Hotel and Conference Center](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/8b8d1fb3_y.jpg) ### Fort William Henry Hotel and Conference Center 2/10 Terrible "This establishment's advertising and most reviews certainly create a mismatch between expectations and reality. At a minimum, any usage of words by this establishment to describe themselves as "luxury" or "deluxe" (or any other related synonyms used) are inappropriate. This stay was intended for my wife and I's anniversary. When we checked in, the staff made the interesting comment after telling us our room number, "You can't change rooms." And we asked "What do you mean? We just got here, why would we ask you to change rooms?"... 😅 Little did we know how relevant that would become. Firstly, let's begin by how ridiculous it is that they charge a resort fee for places that weren't open, unavailable, some under construction, and not being allowed to really stay near the resort. The premises features a detached wing on the west thats in worse shape than any common budget hotel chain despite being advertised as "newly renovated". Sincerely, to all readers, there are waterfront views of Lake George in better quality rooms for better prices. But for completeness and transparency, it's important to further illustrate the lackluster quality. I think that recently renovated "resorts" would have a better installation of higher quality flooring. The owners felt it acceptable to use the cheap peel and stick vinyl flooring throughout a large portion of the property--like the cheapest a landlord would ins. In our room in particular, that flooring had started to peel. " [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/8b1d260e_y.jpg) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY 10/10 Excellent "Was a excellent stay I would use them again " [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.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 "Perfect location to ski at Gore and explore Lake George village with hassle-free parking, clean rooms, and good amenities for pets. The breakfast was weak, but staff were super helpful, friendly, and available. Proximity to grocery store made the minimal breakfast not an issue. " [](https://expedia.ca/Lake-George-Hotels-Super-8-By-Wyndham-Lake-GeorgeWarrensburg-Area.h459792.Hotel-Information) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/8795775f_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 8/10 Good "Staff at front desk are horrible and not welcoming at all! Every time we go no service but we have been going for 12 years so we try to ignore the rudeness at front desk " [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ## Find out more about Chestertown ## Chestertown Guest Houses information | Number of reviews | | | ----------------- | -------------- | | Accommodation | 2 Guest Houses | | Lowest Price | CA $153 | | Highest Price | CA $153 | ## 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) - 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