Title: Chestertown Cottages from CA $331 | 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 In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown cottages ![Property grounds](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/c01ec95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/18e42197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/1e1c1bc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/8b542543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Fort Ann [](https://www.expedia.ca/Fort-Ann-Hotels-Waterfront-Cottage-With-Fireplace-20-Min-From-Lake-George.h82945159.Hotel-Information) 10/10 Exceptional (24 reviews) "Wonderful stay at a GREAT property!Couldn't ask for more!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert H. CA $248 CA $508 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Fort-Ann-Hotels-Waterfront-Cottage-With-Fireplace-20-Min-From-Lake-George.h82945159.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120060000/120053000/120052999/6c1e1109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120060000/120053000/120052999/5badaa2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120060000/120053000/120052999/c5516cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120060000/120053000/120052999/b95b3344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Hudson Falls [](https://www.expedia.ca/7-Mi-To-Glens-Falls-Peaceful-Retreat-W-Game-Room.h120052999.Hotel-Information) CA $314 CA $910 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/7-Mi-To-Glens-Falls-Peaceful-Retreat-W-Game-Room.h120052999.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) ![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76660600/76660597/37726a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76660600/76660597/e112bf38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76660600/76660597/f73aed10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in North Creek [](https://www.expedia.ca/North-Creek-Hotels-Beautiful-Cottage-On-Quiet-Country-Road.h76660597.Hotel-Information) 9.8/10 Exceptional (50 reviews) "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 $236 CA $341 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/North-Creek-Hotels-Beautiful-Cottage-On-Quiet-Country-Road.h76660597.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121360000/121352600/121352510/c4392bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121360000/121352600/121352510/6e6c5ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121360000/121352600/121352510/0bb9c89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/122000000/121360000/121352600/121352510/9dcf32c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Hadley [](https://www.expedia.ca/Hadley-Hotels-The-Pine-Ridge-Retreat-A-Cozy-Great-Sacandaga-Cottage-With-Private-Lake-Access.h121352510.Hotel-Information) CA $231 CA $331 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Hadley-Hotels-The-Pine-Ridge-Retreat-A-Cozy-Great-Sacandaga-Cottage-With-Private-Lake-Access.h121352510.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280757/47c9f996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280757/9e6c6264.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280757/w2996h1997x4y2-9f5d7b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280757/93d2bad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Warrensburg [](https://www.expedia.ca/Warrensburg-Hotels-Perfect-Autumn-Getaway.h122280757.Hotel-Information) CA $227 CA $414 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Warrensburg-Hotels-Perfect-Autumn-Getaway.h122280757.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=2026-01-31&endDate=2026-02-01®ionId=89045&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CONDO) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=VILLA) ![](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-Cottages.d89045-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Cottages.d89045-aaCottages.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![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 "Great experience over all" [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.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) ![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 "Staff was super friendly. Room was very clean and just as described . Restaurant was very good with tasty food . " [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.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 "Great hotel the kids love the pool. Hotel is clean staff is friendly. Check in is efficient." [](https://expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.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 "When they say they have a fitness room they have a fitness room jump box weights bench cardio hot tub was quite enjoyable staff was wonderful breakfast included some gluten-free options vegetarian options which was fantastic vegan options not a time but it's a hotel breakfast rooms were clean comfortable we had a king for two people it was more than enough right near downtown lake George very walkable near Shepherd's Park and absolutely great stay" [](https://expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Yes and the hotel was beautifully decorated " [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.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 "Its always GREAT to see Nakita behind the desk!! So welcoming and remembers return customers. The place is very clean and comfortable! This is always our go to place!" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![North Creek Lodge at Gore Mountain](https://images.trvl-media.com/lodging/8000000/7520000/7510500/7510444/29d03cb5_y.jpg) ### North Creek Lodge at Gore Mountain 10/10 Excellent "Lovely owners. So kind and gracious." [](https://expedia.ca/Lake-George-Hotels-Black-Mountain-Lodge.h7510444.Hotel-Information) ![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d_y.jpg) ### Eagles Nest at Loon Lake near Gore Mountain 10/10 Excellent "We had a great Christmas gateway at the Eagle’s Nest. Plenty of room for our extended family to sleep, dine, and hang out. " [](https://expedia.ca/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) ## Find out more about Chestertown ## Chestertown Cottages information | Number of reviews | 74 | | ----------------- | ------------ | | Accommodation | 159 Cottages | | Lowest Price | CA $331 | | Highest Price | CA $910 | ## Frequently asked questions ### How much do cottages in Chestertown cost? ### How many cottages are there in Chestertown? ### Are there any family-friendly cottages in Chestertown? ### Why book your cottage in Chestertown with Expedia? ### How can I find cheap cottages in Chestertown? ### What is there to do in Chestertown near my cottage? ## 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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