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 ![Aerial view of Hudson River in upstate New York, Chestertown, Riparius Bridge. July 12, 2022](https://images.trvl-media.com/place/89045/d8935802-94c8-4419-b7bf-ae82c253406c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## 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 ![The Fern Lodge](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Fern Lodge 46 Fiddlehead Bay Rd. Chestertown NY Book a stay at this beach B&B in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Friends Lake and Loon Lake Beach are located ... 10/10 Exceptional! (52 reviews) I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! Reviewed on Dec 27, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=1538972&PinnedHotelID=1538972&HadPinnedHotel=true®ionId=89045) [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=1538972&PinnedHotelID=1538972&HadPinnedHotel=true®ionId=89045) ![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eagles Nest at Loon Lake near Gore Mountain Chestertown NY 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 ... [Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true®ionId=89045) [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true®ionId=89045) ![Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.](https://images.trvl-media.com/lodging/121000000/120760000/120755100/120755074/be8d3406_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure. Chestertown NY Stay at this vacation home in Chestertown. Enjoy free WiFi, tennis courts, and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ... 10/10 Exceptional! (2 reviews) The host, Bryce, responded in a quick manner whenever we reached out to him. The accommodations were homey, spacious, and it was a quick and easy walk from the parking space to the place. Would definitely stay there again. Reviewed on Feb 8, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=120755074&PinnedHotelID=120755074&HadPinnedHotel=true®ionId=89045) [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=120755074&PinnedHotelID=120755074&HadPinnedHotel=true®ionId=89045) [See all 1,536 properties in Chestertown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026®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. ![Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.](https://images.trvl-media.com/lodging/121000000/120760000/120755100/120755074/be8d3406_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure. Chestertown NY Stay at this vacation home in Chestertown. Enjoy free WiFi, tennis courts, and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ... 10/10 Exceptional! (2 reviews) The host, Bryce, responded in a quick manner whenever we reached out to him. The accommodations were homey, spacious, and it was a quick and easy walk from the parking space to the place. Would definitely stay there again. Reviewed on Feb 8, 2026 [](https://expedia.ca/Chestertown-Hotels-Secluded-And-Cozy-Lakeside-Townhome-On-Tripp-Lake.h120755074.Hotel-Information) ![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eagles Nest at Loon Lake near Gore Mountain Chestertown NY 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 ... [](https://expedia.ca/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) ![Charming 4 Bedroom Home In Lake Luzerne. 10 miles to Lake George Village.](https://images.trvl-media.com/lodging/34000000/33580000/33570300/33570223/42334a87_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Charming 4 Bedroom Home In Lake Luzerne. 10 miles to Lake George Village. Lake Luzerne NY Book a stay at this family-friendly vacation home in Lake Luzerne. Enjoy laundry facilities, a pool table, and patios. Our guests praise the helpful staff in ... 10/10 Exceptional! (216 reviews) This property is fantastic. Sooooo much room 4 spacious bedrooms. One n the lower floor is a full suite. We went with my whole family. 1 couple and 1 year old in bottom floor suite, 2 adult kids if n the bunk room and 1 adult child in huge master. Parents on second floor with our own bathroom. 3 ... Reviewed on Mar 3, 2026 [](https://expedia.ca/Lake-George-Hotels-Charming-4-Bedroom-Home-In-Lake-Luzerne.h33570223.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 [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-03-24&endDate=2026-03-25)[Mar 24 - Mar 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-03-24&endDate=2026-03-25) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-03-25&endDate=2026-03-26)[Mar 25 - Mar 26](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-03-25&endDate=2026-03-26) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026)[Mar 27 - Mar 29](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[Apr 3 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026) ### Popular places to visit ![Loon Lake](https://images.trvl-media.com/place/553248635976196050/b1196dfe-0b1b-43de-9b4b-94dcffab0606.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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) #### 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 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 ![August 20 2024, Sunny afternoon summer aerial image of the area surrounding Bolton Landing, NY, USA and Lake George.](https://images.trvl-media.com/place/55597/c1cee649-2a4e-4ab8-8a25-4dfebb2ecf85.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Bolton Landing ![USA, New York State. View from Crane Mountain, Adirondack Mountains.](https://images.trvl-media.com/place/6349362/b2a53b82-0bfe-4d13-a0ee-f548f109f5ac.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Johnsburg ![Colorful Autumn Forest in Adirondacks from Above](https://images.trvl-media.com/place/6349845/f05cf8e5-64d7-4f1f-80fc-07e236774ef7.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Pottersville - 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) - [Wild West Ranch and Western Town ](https://expedia.ca/Wild-West-Ranch-And-Western-Town-Lake-George.d6171522.Vacation-Attraction) - [Adirondack Outlet Mall ](https://expedia.ca/Adirondack-Outlet-Mall-Lake-George.d6173782.Vacation-Attraction) - [Hearthstone Point Campground ](https://expedia.ca/Hearthstone-Point-Campground-Lake-George.d553248621579082980.Vacation-Attraction) - [House of Frankenstein Wax Museum ](https://expedia.ca/House-Of-Frankenstein-Wax-Museum-Lake-George.d6064461.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. 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