Title: Book the Best Hotels with BARS in Chestertown in 2026 | 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 Hotels with Bar in Chestertown, NY from CA $148 - ![](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 Hotels with Bar ## Top Chestertown Hotels with Bar ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/4c20fc37.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) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/5b03322e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/4dfecf21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/a7d54fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Lake George - Adirondack Area by IHG Lake George 9.2/10 Wonderful (1001) "We enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audrey CA $133 CA $148 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Room, Multiple Beds, Lake View (Balcony)](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/6dc91933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/e9dffaf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/4d9439b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Lake George Lake George 9.2/10 Wonderful (1000) "Loved my stay, the room was comfy and nice and clean, plenty to do right in the hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie CA $162 CA $180 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/a91c67c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Queensbury Hotel Glens Falls 9.4/10 Exceptional (1452) "We loved our stay here!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph [](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) ![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) ![Reception](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/aaafa0c7.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) ### Hampton Inn & Suites Lake George Lake George 8.8/10 Excellent (1000) "Excellent and friendly service from reception to housekeeping to restaurant staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $134 CA $149 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/8000000/7520000/7510500/7510444/29d03cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/8000000/7520000/7510500/7510444/efe49124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7520000/7510500/7510444/4f4a927f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/8000000/7520000/7510500/7510444/9142b6db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Creek Lodge at Gore Mountain North Creek 8.0/10 Very good (402) "Mattresses were incredibly comfortable, room felt clean. Only thing we did not like was that there was not a deadbolt on the door. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $170 CA $188 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Lake-George-Hotels-Black-Mountain-Lodge.h7510444.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/4df3b4c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/a8a5ec23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/e8c3fc23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Six Flags Great Escape Lodge & Indoor Waterpark Queensbury 7.8/10 Good (1392) "Me and family enjoyed our time." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Emilie CA $166 CA $184 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![Premium Chalet, Multiple Beds | Terrace/patio](https://images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/060fd21f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 1 Queen Bed](https://images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/8e37493d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/ff51d882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, kayaking, motor boating](https://images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/8459efd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lodge at Schroon Lake Schroon Lake 9.0/10 Wonderful (412) "Nice restaurant- welcoming staff, good live music! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $185 CA $255 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Schroon-Lake-Hotels-Lodge-At-Schroon-Lake.h92466918.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/59b5e6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/3dd62919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/ff93fb28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fort William Henry Hotel and Conference Center Lake George 8.4/10 Very good (1003) "Clean room great customer service and the grounds were great for the Lake" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ROBERT CA $176 CA $223 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Lunch, dinner served; German cuisine, garden views ](https://images.trvl-media.com/lodging/9000000/8380000/8378700/8378633/5482b498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds | View from room](https://images.trvl-media.com/lodging/9000000/8380000/8378700/8378633/a9ce9a45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/9000000/8380000/8378700/8378633/83552bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden views, open select days](https://images.trvl-media.com/lodging/9000000/8380000/8378700/8378633/b6cfd5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gore Mountain Lodge North Creek 9.2/10 Wonderful (211) "hi, everything was great, would go back again, great location!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) david CA $238 CA $264 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Lake-George-Hotels-Gore-Mountain-Lodge.h8378633.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=2025-12-16&endDate=2025-12-17®ionId=89045&adults=2&amenities=BAR&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 ![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 "Quiet, clean, comfortable, excellent staff." [](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 "Staff are super friendly, and there are many things to do at the hotel to have fun." [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Wonderful hotel, with lots of old charm!" [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.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) ![Lodges At Cresthaven](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/4993b753_y.jpg) ### Lodges At Cresthaven 10/10 Excellent "Great !" [](https://expedia.ca/Lake-George-Hotels-Lodges-At-Cresthaven.h1320727.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 "Fantastic breakfast and very accommodating staff. Very clean and cozy " [](https://expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.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) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Everyone was so nice and welcoming Room is clean Convenient location Restaurant food was delicious " [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Fort William Henry Hotel and Conference Center](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Everything good - a continental breakfast would be nice - maybe just real milk for coffee & pastries & oatmeal? " [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Chestertown? > Chestertown features 113 hotels and other accommodations to choose from, and likely many will have a bar where you can enjoy an evening cocktail after a day out exploring. While you're here, you can check out Loon Lake Beach and Friends Lake. ### What are the best hotels with bars in Chestertown? > Here's some of the top Chestertown accommodations with bars: [Friends Lake Inn](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [The Fern Lodge](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information): Enjoy the bar, free breakfast, and free WiFi. ### What is there to do in Chestertown? > Consider a visit to Loon Lake Beach, Friends Lake, and Loon Lake, and then find a cozy spot for a nightcap. Other places to see include Hudson River and Tripp Pond. Chestertown is known for its lakeside. ### When is the best time to visit Chestertown? > Visiting local bars in Chestertown is more fun when you know what the weather holds. These rainfall averages and temperatures can help you determine the best time for bar hopping. 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. ### How can I get to Chestertown and around the area? > Here are some of your transportation options in and around Chestertown: Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) away from the heart of the city. 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