Title: Book the Best Chestertown FAMILY FRIENDLY Hotels from CA $116 - 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 $116 ![](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 Family Hotels Tonight [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Chestertown Family Hotels ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/19000000/18960000/18955400/18955323/ac1cd329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18960000/18955400/18955323/05207c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18955400/18955323/0c5915e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18955400/18955323/664ab8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lily Pad at Loon Lake near Gore Mountain Chestertown 9.6/10 Exceptional (39) "Comfortable stay with extended family. Would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pam V. CA $209 CA $619 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chestertown-Hotels-The-Lily-Pad-At-Loon-Lake-Near-Gore-Mountain.h18955323.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/45ba61c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/ddbc1bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/48e94cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/c695ec16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom Chestertown 10/10 Exceptional (1) "Very comfortable!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim K. CA $239 CA $656 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Chestertown-Hotels-Cozy-3BR-35BA-Lodge-W-Lake-Beach-Access.h119689867.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/b0a450bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/2f2dc01c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/66a73c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/133f198e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY Queensbury 9.0/10 Wonderful (1265) "Friendly staff...clean rooms comfy beds great hotel great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tarah CA $123 CA $136 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Private beach, beach volleyball, sailing, kayaking](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/9205018c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/f27894c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/dddb7afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/72d8a398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Bay YMCA Inn and Conference Center Silver Bay 8.8/10 Excellent (131) "Awesome place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $132 CA $146 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Silver-Bay-Hotels-Silver-Bay-Inn-And-Conference-Center.h96493210.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/558e7d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/cd5678ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/ffb6051c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/5389bae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Lake George Lake George 9.0/10 Wonderful (1711) "Great place for a weekend to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $135 CA $150 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/01f531cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Accessible (Hotel Single Queen)](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/4d6605cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/75b79163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Queensbury Hotel Glens Falls 9.4/10 Exceptional (1396) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra [](https://www.expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/201ef456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/9e99e079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, One King Bed, Non-Smoking | Living area](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/98f82ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/7a626a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Lake George Lake George 8.8/10 Excellent (1001) "Very pet friendly!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $136 CA $151 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/5000000/4580000/4572000/4571987/daeeb60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/5000000/4580000/4572000/4571987/dc44b8fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4580000/4572000/4571987/5efb0d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4580000/4572000/4571987/c4825ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lake George Lake George 8.0/10 Very good (1005) "Great staff and location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $105 CA $116 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Lake-George-Hotels-Howard-Johnson-By-Wyndham-Lake-George.h4571987.Hotel-Information) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1610000/1608000/1607966/1b401302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1610000/1608000/1607966/1980b00e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily breakfast](https://images.trvl-media.com/lodging/2000000/1610000/1608000/1607966/cb046cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1610000/1608000/1607966/032a0be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Queensbury 7.8/10 Good (1000) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $105 CA $117 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Queensbury-Hotels-Quality-Inn.h1607966.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11960000/11958100/11958004/7c445aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11960000/11958100/11958004/2dce92ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 2 Bedrooms, 2 Bathrooms](https://images.trvl-media.com/lodging/12000000/11960000/11958100/11958004/w1242h889x0y5-65aecaab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11958100/11958004/06a33678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luzerne Court Motel Lake Luzerne 9.4/10 Exceptional (317) "This is our second time staying here and it was just perfect for our weekend getaway." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Tracy CA $152 CA $169 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Lake-George-Hotels-Luzerne-Court-Motel.h11958004.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=2025-11-13&endDate=2025-11-14®ionId=89045&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Fort William Henry Hotel and Conference Center](//images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Beautiful area, nice room" [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.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 "we enjoyed the happy hour with a glass of wine and a beer with nachos. Food was great. I would have enjoyed the wine more if it was in a glass, vs a plastic cup. Service was great and the staff was friendly." [](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information) ![The Queensbury Hotel](//images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Beautiful, clean, comfortable stay. The pub had great service, food and waitstaff. Breakfast was delicious and great service. Wonderful location and easy to walk to other places downtown. We will be back!❤️" [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Comfort Inn & Suites Lake George](//images.trvl-media.com/lodging/2000000/1650000/1640200/1640103/93d3500a_y.jpg) ### Comfort Inn & Suites Lake George 10/10 Excellent "Clean and not crowded, went offseason and almost Empty! Little dated but huge rooms and everything you needed plus breakfast, win-win. I’d go back" [](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.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 "Clean, staff was super friendly and accommodating for children " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.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 "Hotel was maintained and kept in good shape for being an older place." [](https://expedia.ca/Lake-George-Hotels-Clarion-Inn-Suites-At-The-Outlets-Of-Lake-George.h26327.Hotel-Information) ![Admiral Motel](//images.trvl-media.com/lodging/19000000/18530000/18528500/18528423/a3b9e25a_y.jpg) ### Admiral Motel 10/10 Excellent "Besides the bathroom needing to be updated it’s a great place to stay. Very clean. You can walk to the local restaurants. Even though you’re on the main strip it’s very quiet. I stayed for 3 nights and I would stay again. " [](https://expedia.ca/Lake-George-Hotels-Admiral-Motel.h18528423.Hotel-Information) ![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 "The staff was excellent. The room was immaculate. Overall, a great stay." [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Courtyard by Marriott Lake George](//images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569_y.jpg) ### Courtyard by Marriott Lake George 10/10 Excellent "Room was very clean and spacious! " [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.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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