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Experience the tranquil beauty of the Berkshire Mountains in class and luxury when you stay at one of these outstanding vacation rentals with pools near Lenox, Massachusetts! Embark on a horseback riding adventure in Kennedy Park. Head north to the Pleasant Valley Wildlife Sanctuary and enjoying exploring over 1,000 acres of forests, wetlands, and meadows. Sign up for a guided canoe trip along the Housatonic River. Whether you choose to explore the outdoors on land or water, you'll create fantastic memories when staying near Lenox. Check out the charming cottages, cabins, and other luxurious homes available with pools in the area to get your trip started!