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Check Prices on Hotels in Chestertown

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Top 10 Hotels in Chestertown

See all 342 Properties in Chestertown

Estimated price for 1 night/2 adults

Lily Pad South @ Loon Lake, in the Adirondacks Near Gore Mountain

Lily Pad South @ Loon Lake, in the Adirondacks Near Gore Mountain

Chestertown, New York
Lily Pad South @ Loon Lake, in the Adirondacks Near Gore Mountain
     
     

    This family-friendly Chestertown apartment building is located on a lake, within 3 mi (5 km) of Loon Lake, Schroon Lake and Loon Lake Beach. Friends Lake and ...

    Lily Pad South @ Loon Lake, in the Adirondacks Near Gore MountainGet Rates

    The Loft at The Remington

    The Loft at The Remington

    6369 Main Street, Chestertown, NY
    The Loft at The Remington
      3.5 out of 5.0
       
       

      Situated in Chestertown, this bed & breakfast is within 3 mi (5 km) of Loon Lake, Loon Lake Beach, and Friends Lake. Tripp Pond and Schroon Lake are also within ...

      The Loft at The RemingtonGet Rates

      Friends Lake Inn

      Friends Lake Inn

      963 Friends Lake Rd, Chestertown, NY
      Friends Lake Inn
        4.0 out of 5.0
         
         

        Located in the mountains, this Chestertown hotel offers ski-in/ski-out access within 3 mi (5 km) of Friends Lake and Loon Lake Beach and close to winter sports ...

        Friends Lake Inn$199

        Aug 6 - Aug 7

        Eagles Nest at Loon Lake Near Lake George

        Eagles Nest at Loon Lake Near Lake George

        Chestertown, New York
        Eagles Nest at Loon Lake Near Lake George
           
           

          This family-friendly Chestertown vacation home is located on a lake, within 3 mi (5 km) of Loon Lake, Schroon Lake and Loon Lake Beach. Friends Lake and Natural ...

          Eagles Nest at Loon Lake Near Lake GeorgeGet Rates

          NEW Listing! Historic Greek Revival Style Home Near Attractions!

          NEW Listing! Historic Greek Revival Style Home Near Attractions!

          Chestertown, New York
          NEW Listing! Historic Greek Revival Style Home Near Attractions!
             
             

            Situated in the mountains, this historic vacation home is within 3 mi (5 km) of Loon Lake, Loon Lake Beach, and Friends Lake. Tripp Pond and Schroon Lake are ...

            NEW Listing! Historic Greek Revival Style Home Near Attractions!Get Rates

            The Lily Pad North at Loon Lake, in the Adirondacks Near Gore Mountain

            The Lily Pad North at Loon Lake, in the Adirondacks Near Gore Mountain

            Chestertown, New York
            The Lily Pad North at Loon Lake, in the Adirondacks Near Gore Mountain
               
               

              Located in the heart of Chestertown, this historic apartment building is 0.1 mi (0.1 km) from Loon Lake and within 3 mi (5 km) of Schroon Lake and Loon Lake ...

              The Lily Pad North at Loon Lake, in the Adirondacks Near Gore MountainGet Rates

              NEW Listing! Charming log House With Dock - Walk to Beach Access!

              NEW Listing! Charming log House With Dock - Walk to Beach Access!

              Chestertown, New York
              NEW Listing! Charming log House With Dock - Walk to Beach Access!
                 
                 

                Situated in Chestertown, this vacation home is 0.1 mi (0.1 km) from Loon Lake and 1.8 mi (2.8 km) from Loon Lake Beach. Friends Lake and Schroon Lake are also ...

                NEW Listing! Charming log House With Dock - Walk to Beach Access!Get Rates

                NEW Listing! Dog-friendly, Lakefront Camp Cabin With Dock, Multiple Decks

                NEW Listing! Dog-friendly, Lakefront Camp Cabin With Dock, Multiple Decks

                Chestertown, New York
                NEW Listing! Dog-friendly, Lakefront Camp Cabin With Dock, Multiple Decks
                   
                   

                  Situated on the waterfront, this vacation home is 0.1 mi (0.1 km) from Friends Lake and within 6 mi (10 km) of Loon Lake Beach and Loon Lake. Tripp Pond and ...

                  NEW Listing! Dog-friendly, Lakefront Camp Cabin With Dock, Multiple DecksGet Rates

                  NEW Listing! Cozy Cottage With Deeded Lake Rights - 100 Steps to the Beach

                  NEW Listing! Cozy Cottage With Deeded Lake Rights - 100 Steps to the Beach

                  Chestertown, New York
                  NEW Listing! Cozy Cottage With Deeded Lake Rights - 100 Steps to the Beach
                     
                     

                    Situated on the waterfront, this vacation home is within a 15-minute walk of Loon Lake and Loon Lake Beach. Friends Lake is 2.2 mi (3.5 km) away.

                    NEW Listing! Cozy Cottage With Deeded Lake Rights - 100 Steps to the BeachGet Rates

                    NEW Listing! Lakefront, 3-level House on a Cove With Beach & Large Dock

                    NEW Listing! Lakefront, 3-level House on a Cove With Beach & Large Dock

                    Chestertown, New York
                    NEW Listing! Lakefront, 3-level House on a Cove With Beach & Large Dock
                       
                       

                      This family-friendly Chestertown vacation home is located on the waterfront, within 1 mi (2 km) of Loon Lake and Loon Lake Beach. Friends Lake and Schroon Lake ...

                      NEW Listing! Lakefront, 3-level House on a Cove With Beach & Large DockGet Rates

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