If you're looking to discover somewhere new, look no further than Chestertown. Whether you're planning to stay for a night or for the week, the area around Chestertown has accommodations to fit every need. Search for hotels in Chestertown with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Chestertown hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Chestertown hotel deals are here with our lowest price guarantee.
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Hotels in Chestertown
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Pine Tree Motel & Cabins
Pine Tree Motel & Cabins
9.2 out of 10, Wonderful, (127)
The price is CA $238
CA $264 total
includes taxes & fees
Jul 7 - Jul 8
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.
Go beyond your typical stay in Chestertown
Pet friendly
Top neighborhoods in Chestertown
Chester Shores
Chestertown's Chester Shores neighborhood offers attractions including Loon Lake.
Top landmarks in Chestertown
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.
Learn more about Chestertown
Chestertown is well-known for its attractions such as Loon Lake Beach and Friends Lake. The city has something for everyone including sights like Loon Lake and Hudson River within a secluded setting.

Photo by Julie Miller
Open Photo by Julie Miller
Check out the Chestertown hotels guests love right now

La Quinta Inn & Suites by Wyndham Lake George
10/10 Excellent
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- Hotels near Six Flags Great Escape
- Hotels near Friends Lake
- Hotels near Loon Lake
- Hotels near Loon Lake Beach
- Hotels near Tripp Pond
- Hotels near Million Dollar Beach
- Hotels near Lake George Steamboat Company
- Hotels near Outlets at Lake George
- Hotels near Fort William Henry Museum
- Hotels near Gore Mountain Ski Resort
- Hotels near Shepard's Beach Park
- Hotels near Lake George Dog Beach
- Hotels near The Sagamore Golf Club
- Hotels near Adirondack Outlet Mall
- Hotels near Adirondack Winery
- Hotels near Lake George Shoreline Cruises
- Hotels near Cool Insuring Arena
- Hotels near Wild West Ranch and Western Town
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