Title: Book the Best CHEAP Hotels in Chestertown, NY - Chestertown Cheap Hotels | 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 Cheap Hotels in Chestertown, NY - ![](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 Cheap Hotels Tonight [Nov 28 - Nov 29](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-28&endDate=2025-11-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Tomorrow [Nov 29 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-29&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) ## Top Chestertown Cheap Hotels ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/1b13c3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/3a2c4196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/0a784cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Friends Lake Inn Chestertown 8.6/10 Excellent (102) "Friendly staff, room was clean, well maintained. Ate at the restaurant, food was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin [](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information) ![Lake view](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/698049bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Double Room, Hot Tub, Lake View (Oak)](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/52ace6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/7d1b588f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Fern Lodge Chestertown 9.8/10 Exceptional (50) "Absolutely beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.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=2025-12-12&endDate=2025-12-13®ionId=89045&adults=2&travelerType=budget_property&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_89045) ## Top Chestertown Hotel Reviews ![Baymont by Wyndham Queensbury / Lake George](https://images.trvl-media.com/lodging/1000000/30000/23700/23630/cf943129_y.jpg) ### Baymont by Wyndham Queensbury / Lake George 10/10 Excellent "room was clean " [](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.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 "Beautiful property close to everything. I booked the room with the balcony and it was just like the pictures. We had dinner at restaurant in the hotel, the food was delicious and great service. Room was very clean and comfortable. We are looking forward to returning in the Spring. " [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.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 "Room was very clean, comfortable bed and nice bedding, large bathroom with good amenities." [](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 "The room was clean. Staff were courteous and friendly. " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.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 "Staff was super friendly, even remembering us (or more likely our dog!). Room was very clean, bathroom looked like it had been recently updated. (Previous stays had very tired looking bathroom.) Coffee and breakfast bar was actually ready at 6, unlike at other hotels. Coffee was rather good! And actual Half n Half pods were available. Oh, and bonus: they now provide poop bags for picking up after your fur baby. Nice touch! If you go, ask for Rebel, behind the desk. A happy, sweet capuccino colored pitty who wobbles but doesn't fall down (usually), due to a neurological condition. He's a great welcoming comittee of one!" [](https://expedia.ca/Lake-George-Hotels-Super-8-By-Wyndham-Lake-GeorgeWarrensburg-Area.h459792.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) ![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 "Check in was great " [](https://expedia.ca/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.Hotel-Information) ## Frequently asked questions ### What is Chestertown like for travelers on a budget? > Chestertown offers cheap accommodation options and a variety of places to visit, making it a great getaway spot for budget travelers. You can find ways to save money while getting to know this destination, which is home to attractions like Loon Lake Beach, Friends Lake, and Loon Lake. ### When is the best time for a budget trip to Chestertown? > Weather is probably a major factor when you plan your trip to Chestertown, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall. ### What is there to see and do in Chestertown? > Chestertown is known for its lake views and offers things to see and do without spending a fortune. You can budget for the local attractions that interest you most, and then fill your itinerary with activities that cost little or nothing at all. Enjoy the outdoors at Loon Lake Beach and Friends Lake, or check out the area's cultural spots like Tannery Pond Community Center. ### How can I get to Chestertown and get around on a budget? > Scoping out the transportation options in Chestertown is a smart way to keep your trip affordable. The closest airport is Glens Falls, NY (GFL-Floyd Bennett Memorial), situated 23.6 mi (38 km) away. 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