Title: Book the Best HISTORIC Hotels in Chestertown in 2026 | 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 # Find Historic Hotels in Chestertown, NY from CA $164 - ![](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 availability on Chestertown Historic Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown historic hotels ![Room, Multiple Beds, Lake View (Balcony)](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Lake View (Balcony)](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/db6cb3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/e9dffaf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/4d9439b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Lake George [](https://www.expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) Lake George 9.2/10 Wonderful (1000) "Loved my stay, the room was comfy and nice and clean, plenty to do right in the hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie CA $147 CA $164 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![Premium Room](https://images.trvl-media.com/lodging/6000000/5180000/5179400/5179323/c5361517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Bedroom](https://images.trvl-media.com/lodging/6000000/5180000/5179400/5179323/0a92b8c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5180000/5179400/5179323/8fc3ec9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room | Private kitchen](https://images.trvl-media.com/lodging/6000000/5180000/5179400/5179323/1ecb8cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alpine Lodge [](https://www.expedia.ca/Lake-George-Hotels-The-Alpine-Lodge.h5179323.Hotel-Information) North Creek 9.0/10 Wonderful (657) "As described, clean, good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julianne [](https://www.expedia.ca/Lake-George-Hotels-The-Alpine-Lodge.h5179323.Hotel-Information) ![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) ![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) ![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) ### 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 (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) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/7c36798c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/3dd62919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/ff93fb28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fort William Henry Hotel and Conference Center [](https://www.expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) Lake George 8.4/10 Very good (1003) "Clean room great customer service and the grounds were great for the Lake" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ROBERT CA $155 CA $199 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107590000/107580400/107580374/1c1f3ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107590000/107580400/107580374/1258cf4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107590000/107580400/107580374/1c2ed801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107590000/107580400/107580374/a8c01c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Camp RiverWood on the Hudson River [](https://www.expedia.ca/North-Creek-Hotels-Camp-RiverWood-On-The-Hudson-River.h107580374.Hotel-Information) North Creek 9.8/10 Exceptional (6) "Beautiful cabin, clean, great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle D. CA $241 CA $350 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/North-Creek-Hotels-Camp-RiverWood-On-The-Hudson-River.h107580374.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/20000000/19320000/19318000/19317908/7332418d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19320000/19318000/19317908/1162c961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19320000/19318000/19317908/752d40ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19320000/19318000/19317908/75cc202b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR [](https://www.expedia.ca/Lake-George-Hotels-Restored-Historic-Adirondack-Camp-Views-OF-Nearby-Gore-Moutain.h19317908.Hotel-Information) North River 9.2/10 Wonderful (63) "See you next year amazing stay great food loved the bird camp cabin—- Brian, Darlene, Gracie and Hayden " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian W. CA $241 CA $367 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lake-George-Hotels-Restored-Historic-Adirondack-Camp-Views-OF-Nearby-Gore-Moutain.h19317908.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76670000/76660600/76660597/231e7e6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76670000/76660600/76660597/56254e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books](https://images.trvl-media.com/lodging/77000000/76670000/76660600/76660597/ca2079e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76670000/76660600/76660597/6c97fcf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful cottage on quiet country road walking distance to charming North Creek [](https://www.expedia.ca/North-Creek-Hotels-Beautiful-Cottage-On-Quiet-Country-Road.h76660597.Hotel-Information) North Creek 9.8/10 Exceptional (50) "It was a nice place, comfortable, nice location. Could have been cleaner but we had a nice relaxing time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary M. CA $234 CA $341 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/North-Creek-Hotels-Beautiful-Cottage-On-Quiet-Country-Road.h76660597.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/19000000/18600000/18593000/18593000/fcfb357c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, kayaking](https://images.trvl-media.com/lodging/19000000/18600000/18593000/18593000/b6d4d3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Balcony, Lake View](https://images.trvl-media.com/lodging/19000000/18600000/18593000/18593000/ed7ef43a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/19000000/18600000/18593000/18593000/7907f95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surfside On The Lake [](https://www.expedia.ca/Lake-George-Hotels-Surfside-On-The-Lake.h18593000.Hotel-Information) Lake George 8.0/10 Very good (738) "Nice property and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert [](https://www.expedia.ca/Lake-George-Hotels-Surfside-On-The-Lake.h18593000.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34440000/34433300/34433279/e1da3e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34440000/34433300/34433279/d6a4a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/35000000/34440000/34433300/34433279/ff406086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/35000000/34440000/34433300/34433279/18c1370b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake George Water Front Cabin Spectacular Views [](https://www.expedia.ca/Town-Of-Putnam-Hotels-Lake-George-Water-Front-Cabin-Spectacular-Views.h34433279.Hotel-Information) Ticonderoga 9.6/10 Exceptional (35) "Very nice time …. Lake fantastic!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William B. CA $744 CA $1,555 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Town-Of-Putnam-Hotels-Lake-George-Water-Front-Cabin-Spectacular-Views.h34433279.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30330000/30326600/30326566/9055a494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30330000/30326600/30326566/97d18ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30330000/30326600/30326566/c7efaf76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30330000/30326600/30326566/656397e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious ADK 5BR Lodge, Sleeps 14, Near Gore, Firepit, Fireplace, Pets [](https://www.expedia.ca/Wevertown-Hotels-Dog-Friendly-Family-Retreat-Cabin-WGore-Mt-Views.h30326566.Hotel-Information) North Creek 10/10 Exceptional (29) "Lots of room and beautiful cabin" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa M. CA $544 CA $1,309 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Wevertown-Hotels-Dog-Friendly-Family-Retreat-Cabin-WGore-Mt-Views.h30326566.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=2025-12-26&endDate=2025-12-27®ionId=89045&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## 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 "The staff was accomodating and friendly. The room was clean. I have never had a bad stay at this hotel. Plenty of options for breakfast. This hotel is really a "home away from home" kind of place!!" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Wonderfully friendly and helpful staff, great historic hotel with old world service, great location and wonderful food options. All at a very fair price, Hadn’t been here in a while and it’s better than ever. Plan to return in two weeks." [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.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 "It was it was fun " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.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) ![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) ![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 "Everyone was so nice and welcoming Room is clean Convenient location Restaurant food was delicious " [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![The Georgian Lakeside Resort](https://images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/f69be4ef_y.jpg) ### The Georgian Lakeside Resort 10/10 Excellent "The room was spotless, bed & pillows were comfortable. We arrived at night and were surprised at that great view in the morning! My teenagers appreciated the list of channels and the good wi-fi connection. We all recommend ++ " [](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Chestertown? ### How many historical hotels are located in Chestertown? ### What are the must-see historical sites and other places to visit in Chestertown? ### What is a historic hotel like in Chestertown? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Chestertown have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Beach Hotel Hotels in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Beach-Hotel.0-0-d6349269-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Cheap-Hotels.0-0-d6349269-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Family-Hotel.0-0-d6349269-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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