Title: Book the Best Hotels with BARS in Chestertown in 2025 | 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 Hotels with Bar in Chestertown, NY from CA $142 ![](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 ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/65af6a05.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 8.6/10 Excellent (102) "Staff was great. The inn is unique. Perfect!" CA $313 CA $347 total includes taxes & fees Oct 15 - Oct 16 [](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) ![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) ![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) ### The Fern Lodge Chestertown 9.8/10 Exceptional (47) "Comfortable, friendly, beautiful lodge, spacious facilities" CA $574 CA $638 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.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) ![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 (1385) "Great place to stay. " CA $131 CA $146 total includes taxes & fees Oct 30 - Oct 31 [](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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/9e99e079.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) ### Hampton Inn & Suites Lake George Lake George 8.8/10 Excellent (1013) "Very pet friendly!" CA $128 CA $142 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/80e9c724.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) ### Holiday Inn Resort Lake George - Adirondack Area by IHG Lake George 9.2/10 Wonderful (1015) "Clean, great amenities, softttttt sheets!" CA $134 CA $148 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Suite, Lake View | Lake view](https://images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/f69be4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/1fc13319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, Multiple Beds, Lake View | Lake view](https://images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/956c0868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/5007095e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Georgian Lakeside Resort Lake George 8.6/10 Excellent (1009) "I had a great stay!" CA $145 CA $161 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/19000000/18600000/18593000/18593000/fcfb357c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/19000000/18600000/18593000/18593000/7907f95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, kayaking](https://images.trvl-media.com/lodging/19000000/18600000/18593000/18593000/b6d4d3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/19000000/18600000/18593000/18593000/9ed092a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surfside On The Lake Lake George 8.0/10 Very good (720) "Very nice too , loved 3rd floor balcony " CA $129 CA $178 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Lake-George-Hotels-Surfside-On-The-Lake.h18593000.Hotel-Information) ![Room, Non Smoking, Lake View (Balcony, 2 King Beds)](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/6dc91933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking, Lake View (Balcony)](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/db6cb3e0.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) ### Courtyard by Marriott Lake George Lake George 9.2/10 Wonderful (1009) "Great place to stay for enjoying the Lake George area." CA $167 CA $185 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/11000000/10130000/10128900/10128851/0c2b60c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/11000000/10130000/10128900/10128851/d1f2976a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach volleyball](https://images.trvl-media.com/lodging/11000000/10130000/10128900/10128851/ccd08ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/11000000/10130000/10128900/10128851/4de518e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scotty's Lakeside Resort Lake George 8.6/10 Excellent (969) "Very nice stay" CA $139 CA $154 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Lake-George-Hotels-Scottys-Lakeside-Resort.h10128851.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) ![Indoor pool](https://images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/80567dc4.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) ![Exterior](https://images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/ff51d882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lodge at Schroon Lake Schroon Lake 9.0/10 Wonderful (393) "Beautiful property. We had a great stay!" CA $167 CA $232 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Schroon-Lake-Hotels-Lodge-At-Schroon-Lake.h92466918.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=2025-10-28&endDate=2025-10-29®ionId=89045&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![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 "Clean room Very pleasant stsy" [](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.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 "Great" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.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 "Quality of beds were very good" [](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.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 "Clean, great amenities, softttttt sheets!" [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![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 "Excellent hotel. Just stayed too short. " [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.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 "Easy and friendly only complaint is one of the restaurants the food was disgraceful after waiting to get food to go to get back to the room it was inedible . " [](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 "Very spacious clean would absolutely stay there again " [](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information) ![Howard Johnson by Wyndham Lake George](//images.trvl-media.com/lodging/5000000/4580000/4572000/4571987/daeeb60e_y.jpg) ### Howard Johnson by Wyndham Lake George 10/10 Excellent "While not a 5 star hotel, the room and hotel was spotless. Service was excellent and bed was comfortable. We like the fact it was so close to everything. This will be our new go to place for Lake George" [](https://expedia.ca/Lake-George-Hotels-Howard-Johnson-By-Wyndham-Lake-George.h4571987.Hotel-Information) ![The Queensbury Hotel](//images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Old hotel remodeled Very nice" [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Chestertown? > Chestertown features 118 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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