Title: Visit Chestertown: Best of Chestertown Tourism | Expedia Travel Guide - 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) # Chestertown ## Travel Guide ![Photo by Julie Miller](https://mediaim.expedia.com/destination/2/db61c46cb1c1e36f625f3b3e306714b5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Julie Miller](https://mediaim.expedia.com/destination/2/db61c46cb1c1e36f625f3b3e306714b5.jpg) ## Visit Chestertown Where to stay Things to do ### Where to stay in Chestertown ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Chester Shores When in Chester Shores, you can plan a visit to Loon Lake Beach and Loon Lake, some noteworthy sights in the nearby area. [](https://expedia.ca/Chestertown-Chester-Shores.dx553248635976471458) - Chestertown Hotel Deals - Vacation Rentals in Chestertown ![Pine Tree Motel & Cabins](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/29c27732_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pine Tree Motel & Cabins 5537 State Route 8, Chestertown, NY CA $244 CA $271 total Oct 7 - Oct 8 includes taxes & fees Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Loon Lake Beach and Loon Lake are located ... 9.2/10 Wonderful! (141 reviews) "Came here for the weekend with my husband and my dog! The place is really nice, clean" Reviewed on Sep 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F10%2F2025&endDate=08%2F10%2F2025&selected=8355292&PinnedHotelID=8355292&HadPinnedHotel=true®ionId=89045) ![Friends Lake Inn](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Friends Lake Inn 963 Friends Lake Rd, Chestertown, NY CA $311 CA $345 total Oct 7 - Oct 8 includes taxes & fees Stay at this 4-star hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Friends Lake and Loon Lake Beach are located ... 8.6/10 Excellent! (102 reviews) "Staff was great. The inn is unique. Perfect!" Reviewed on Sep 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F10%2F2025&endDate=08%2F10%2F2025&selected=9675030&PinnedHotelID=9675030&HadPinnedHotel=true®ionId=89045) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Queensbury Hotel 88 Ridge St, Glens Falls, NY CA $131 CA $145 total Oct 30 - Oct 31 includes taxes & fees Stay at this 3-star business-friendly hotel in Glens Falls. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in ... 9.2/10 Wonderful! (1,368 reviews) "Wow! What a well-kept grand old hotel. Jennifer Anne at the front desk was welcoming and very helpful. Everyone working here were pleasant I would recommend staying at this hotel." Reviewed on Oct 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&selected=40334&PinnedHotelID=40334&HadPinnedHotel=true®ionId=89045) [See all 1,549 properties in Chestertown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=07%2F10%2F2025&endDate=08%2F10%2F2025®ionId=89045) 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. ![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/24568ce8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eagles Nest at Loon Lake near Gore Mountain Chestertown Book a stay at this family-friendly vacation home in Chestertown. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Loon Lake and Loon ... 9.8/10 Exceptional! (110 reviews) "Cozy home in the Adirondacks. It had everything we needed for 19 relatives for a family reunion." Reviewed on Sep 11, 2025 [](https://expedia.ca/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) ![Lincoln Log Colony](https://images.trvl-media.com/lodging/115000000/114120000/114119400/114119391/fefad528_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lincoln Log Colony 2180 U.S. 9, Lake George, NY Stay at this cabin in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Six Flags Great Escape and Lake George Forum are located ... 9/10 Wonderful! (6 reviews) "Clean room. Great price. Close to everything. Would book again." Reviewed on Sep 6, 2025 [](https://expedia.ca/Lake-George-Hotels-Lincoln-Log-Colony.h114119391.Hotel-Information) ![Waterfront Home on Lake George w/ Boat Dock!](https://images.trvl-media.com/lodging/95000000/94960000/94956700/94956668/d3ff18a8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Home on Lake George w/ Boat Dock! Queensbury Stay at this 3-star cottage in Queensbury. Enjoy free parking, patios, and air conditioning. Popular attractions Assembly Point and Dark Bay are located ... [](https://expedia.ca/New-Waterfront-Home-On-Lake-George-W-Boat-Dock.h94956668.Hotel-Information) [See all properties in Chestertown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=89045&sort=VACATION_RENTAL) 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. ## Check Chestertown hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-06&endDate=2025-10-07) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-06&endDate=2025-10-07) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-06&endDate=2025-10-07) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-06&endDate=2025-10-07)[Oct 6 - Oct 7](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-06&endDate=2025-10-07) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-07&endDate=2025-10-08) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-07&endDate=2025-10-08) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-07&endDate=2025-10-08) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-07&endDate=2025-10-08)[Oct 7 - Oct 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2025-10-07&endDate=2025-10-08) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)[Oct 10 - Oct 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025)[Oct 17 - Oct 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) ### Popular places to visit #### Friends Lake Commune with nature and explore the great outdoors at Friends Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside. [](https://expedia.ca/Friends-Lake-Lake-George.d553248635976195601.Vacation-Attraction) #### Loon Lake Commune with nature and explore the great outdoors at Loon Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside. [](https://expedia.ca/Loon-Lake-Lake-George.d553248635976196050.Vacation-Attraction) #### Loon Lake Beach If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside. [](https://expedia.ca/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction) ## Cities near Chestertown ![Photo by Carla Graichen](https://mediaim.expedia.com/destination/2/52cbecf8d47f1077e91a74ffb7ba7617.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Bolton Landing [](https://expedia.ca/Bolton-Landing.dx55597) ![Photo by Geo M](https://mediaim.expedia.com/destination/2/0ae2c264c1b5c2b4cd7e9c144418a8d7.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Pottersville [](https://expedia.ca/Pottersville.dx6349845) - Cities near Chestertown - Places of interest [Bolton Landing](https://expedia.ca/Bolton-Landing.dx55597)[Diamond Point](https://expedia.ca/Diamond-Point.dx183662)[Johnsburg](https://expedia.ca/Johnsburg.dx6349362)[Pottersville](https://expedia.ca/Pottersville.dx6349845) - [Loon Lake Beach](https://expedia.ca/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction) - [Six Flags Great Escape](https://expedia.ca/Six-Flags-Great-Escape-New-York.d6064469.Vacation-Attraction) - [Gore Mountain Ski Resort](https://expedia.ca/Gore-Mountain-Ski-Resort-North-Creek.d6326108.Vacation-Attraction) - [Outlets at Lake George](https://expedia.ca/Outlets-At-Lake-George-Lake-George.d6210494.Vacation-Attraction) - [Shepard's Beach Park](https://expedia.ca/Shepards-Beach-Park-Lake-George.d553248621554160470.Vacation-Attraction) - [Adirondack Outlet Mall](https://expedia.ca/Adirondack-Outlet-Mall-Lake-George.d6173782.Vacation-Attraction) - [Wild West Ranch and Western Town](https://expedia.ca/Wild-West-Ranch-And-Western-Town-Lake-George.d6171522.Vacation-Attraction) - [Hearthstone Point Campground](https://expedia.ca/Hearthstone-Point-Campground-Lake-George.d553248621579082980.Vacation-Attraction) - [Prospect Mountain](https://expedia.ca/Prospect-Mountain-Lake-George.d6064459.Vacation-Attraction) - [Dr. Morbid's Haunted House](https://expedia.ca/Dr-Morbids-Haunted-House-Lake-George.d6326446.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)