Home to one of the oldest cottages in the 1,000 Islands, Whiskey Island welcomes you and your pooch to experience a piece of history. First built in 1875, this island cottage in Clayton, NY, has been the backdrop for vibrant sunsets and vast stargazing sessions for generations. Explore just over 3 acres of land with your pooch, swim or fish in the river together, and feel the rejuvenating properties of the isolated home. In addition to the grand lodge with a library and five porches, other buildings include a guesthouse, boathouse and skiff house. You’ll need your own boat to stay here. Whiskey Island sleeps 15, and dogs can stay for a $250 pet fee.