Title: Chestertown Cottages from CA $291 | 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 [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-06-26&endDate=2026-06-28&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) ![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) ![Dining](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/0a9e241b.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) ### Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome! [](https://www.expedia.ca/Fort-Ann-Hotels-Waterfront-Cottage-With-Fireplace-20-Min-From-Lake-George.h82945159.Hotel-Information) Fort Ann 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 $249 CA $504 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Fort-Ann-Hotels-Waterfront-Cottage-With-Fireplace-20-Min-From-Lake-George.h82945159.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/f73aed10.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/77000000/76670000/76660600/76660597/37726a2a.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 (51 reviews) "It was exactly what I needed. Quiet and conveniently located for my plans. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ruth A. CA $197 CA $291 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/North-Creek-Hotels-Beautiful-Cottage-On-Quiet-Country-Road.h76660597.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) ![Interior](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280757/w2996h1997x4y2-9f5d7b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280757/ad7c4162.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) ### Convenient location for adventures in the Adirondacks! [](https://www.expedia.ca/Warrensburg-Hotels-Perfect-Autumn-Getaway.h122280757.Hotel-Information) Warrensburg CA $222 CA $413 total includes taxes & fees Mar 10 - Mar 11 [](https://www.expedia.ca/Warrensburg-Hotels-Perfect-Autumn-Getaway.h122280757.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280769/fbf1a98e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280769/69899755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280769/7d94cfd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122290000/122280800/122280769/bc7cbaf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Convenient location for adventures in the Adirondacks! [](https://www.expedia.ca/Warrensburg-Hotels-Perfect-Autumn-Getaway.h122280769.Hotel-Information) Warrensburg CA $274 CA $549 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Warrensburg-Hotels-Perfect-Autumn-Getaway.h122280769.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=2026-03-21&endDate=2026-03-22®ionId=89045&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_89045) ## 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=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&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=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&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=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=COTTAGE) 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=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&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=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&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=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&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=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&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 ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/2f07bb66_y.jpg) ### The Queensbury Hotel 10/10 Excellent "We both loved our stay at the Queensbury hotel! The room was spotless and very nicely decorated. The pool, hot tub and the gym were well kept with good quality treadmills and ample weights to workout. Water and towels were provided. We would definitely go back." [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![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 "Gentleman that checked us in was extremely friendly! Our room was super nice and the pool area was fun 🙂 Breakfast in the morning was good. Would definitely stay here again! " [](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 8/10 Good "Cool waterparks for the kids they really enjoy, some things needs renovations, great stay in général! " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.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 8/10 Good "Comfortable stay!" [](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 8/10 Good "Friendly staff, clean" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Baymont by Wyndham Queensbury / Lake George](https://images.trvl-media.com/lodging/1000000/30000/23700/23630/f7f9bcac_y.jpg) ### Baymont by Wyndham Queensbury / Lake George 10/10 Excellent "Pool is amazing and staff are very nice and room decent and clean and laundry area was great too 😁" [](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.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 "We've stayed here before, we ski and it is less then 30 min from the mountain. It is always quiet and clean. The staff is friendly." [](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 10/10 Excellent "Excellent hotel with great breakfast" [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Howard Johnson by Wyndham Lake George](https://images.trvl-media.com/lodging/5000000/4580000/4572000/4571987/a6724d88_y.jpg) ### Howard Johnson by Wyndham Lake George 4/10 Poor "Heater is terrible, very loud… Room is cold. Shower was terrible. Never stay there again" [](https://expedia.ca/Lake-George-Hotels-Howard-Johnson-By-Wyndham-Lake-George.h4571987.Hotel-Information) ## Find out more about Chestertown ## Chestertown Cottages information | Number of reviews | 75 | | ----------------- | ------------ | | Accommodation | 159 Cottages | | Lowest Price | CA $291 | | Highest Price | CA $549 | ## 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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