Title: Book the Best Chestertown FAMILY FRIENDLY Hotels from CA $270 - Kid-Friendly Hotels in Chestertown, NY | 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) ![](https://mediaim.expedia.com/destination/2/db61c46cb1c1e36f625f3b3e306714b5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller # Find Family Hotels in Chestertown, NY from CA $270 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Family Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-01&endDate=2025-10-02&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-02&endDate=2025-10-03&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-03&endDate=2025-10-05&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Family Hotels ![Exterior](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/29c27732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/55c4d212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/8220a41e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/07b9acd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Tree Motel & Cabins Chestertown 9.2/10 Wonderful (141) "Excellent location and staff was very friendly." CA $244 CA $270 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Lake-George-Hotels-Pine-Tree-Motel-Cabins.h8355292.Hotel-Information) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127.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) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/3a2c4196.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) ### Friends Lake Inn Chestertown 8.8/10 Excellent (101) "Staff was great. The inn is unique. Perfect!" CA $310 CA $345 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18790000/18786900/18786833/19763bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/19000000/18790000/18786900/18786833/e1355b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18790000/18786900/18786833/16cb2338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18790000/18786900/18786833/7cda3819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lily Pad South at Loon Lake near Gore Mountain Chestertown 9.8/10 Exceptional (48) "We had a great time at the Lily Pad. Spent a day at Lake Placid and another day at Lake George...plus took in some of the sights and enjoyed the nearby beach and kayaksThe place was very nice...we would stay there again" [](https://www.expedia.ca/Chestertown-Hotels-Lily-Pad-South-At-Loon-Lake-Near-Gore-Mountain.h18786833.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 (47) "Comfortable, friendly, beautiful lodge, spacious facilities" CA $705 CA $783 total includes taxes & fees Nov 1 - Nov 2 [](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=2025-10-15&endDate=2025-10-16®ionId=89045&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](//images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/b0a450bb_y.jpg) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY 10/10 Excellent "Very clean and easy to find. Staff was very friendly and helpful. Great info on hotel amenities. Good info on area attractions and activities. Excellent continental breakfast." [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Clarion Inn & Suites at the Outlets of Lake George](//images.trvl-media.com/lodging/1000000/30000/26400/26327/b39bcc22_y.jpg) ### Clarion Inn & Suites at the Outlets of Lake George 10/10 Excellent "Excellent option if you are looking something chip and good locatef" [](https://expedia.ca/Lake-George-Hotels-Clarion-Inn-Suites-At-The-Outlets-Of-Lake-George.h26327.Hotel-Information) ![Lakefront Terrace Resort](//images.trvl-media.com/lodging/1000000/900000/899000/898952/7471e44f_y.jpg) ### Lakefront Terrace Resort 10/10 Excellent "Great staff. Very accommodating " [](https://expedia.ca/Lake-George-Hotels-Lakefront-Terrace-Resort.h898952.Hotel-Information) ![Admiral Motel](//images.trvl-media.com/lodging/19000000/18530000/18528500/18528423/a3b9e25a_y.jpg) ### Admiral Motel 10/10 Excellent "Welcoming staff, nicely located, comfortable room" [](https://expedia.ca/Lake-George-Hotels-Admiral-Motel.h18528423.Hotel-Information) ![Six Flags Great Escape Lodge & Indoor Waterpark](//images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg) ### Six Flags Great Escape Lodge & Indoor Waterpark 10/10 Excellent "Safe" [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![The Georgian Lakeside Resort](//images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/f69be4ef_y.jpg) ### The Georgian Lakeside Resort 10/10 Excellent "Great place! Heated outdoor pool in the Fall! " [](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information) ![Tiki Resort](//images.trvl-media.com/lodging/1000000/50000/43200/43183/5068bb33_y.jpg) ### Tiki Resort 10/10 Excellent "The rooms are very clean, we just stayed the night and didn’t use any other facilities. " [](https://expedia.ca/Lake-George-Hotels-Tiki-Resort.h43183.Hotel-Information) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](//images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Group holiday. Excellent location for exploring the Lake George area. Good restaurant and bar with excellent service. Nice to have a pool. Would recommend. " [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Baymont by Wyndham Queensbury / Lake George](//images.trvl-media.com/lodging/1000000/30000/23700/23630/cf943129_y.jpg) ### Baymont by Wyndham Queensbury / Lake George 10/10 Excellent "The guy at the check in desk was super polite and welcoming. While the styling of the hotel common areas is a little dated, everything is crisp, clean, and well maintained. The color scheme is pleasant and neutral. (None of those horrid burnt orange and red tones that some hotel chains use.) The room is nice, comfortable, clean, and in good repair. Breakfast was okay, nothing amazing. If I need a room in this area again, I'll definitely return." [](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.Hotel-Information) ## Frequently asked questions ### What's Chestertown like for family-friendly vacations? > You might want to consider the remote destination of Chestertown if you've been thinking about a trip for the whole family. The boating, horseback riding, and canoeing are just a few things that make this an attractive vacation spot for families. Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) from the city center. ### When's the best time to book a family-friendly vacation in Chestertown? > 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's there to see and do with your family in Chestertown? > While you are visiting Chestertown, you and the family might want to check out some interesting spots such as Gore Mountain Ski Resort, Blue Line Outdoor Center, and Up Yonda Farm Environmental Education Center. 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