Cook the pasta by boiling salted water, adding pasta, and cooking until al dente. Drain and rinse under cold water.

In a mixing bowl, combine cherry tomatoes, cucumber, red onion, and Kalamata olives. Toss gently.

In a separate bowl, whisk olive oil, red wine vinegar, and oregano to make the dressing.

Fold the cooked pasta into the vegetable mixture, and drizzle with the dressing. Toss to combine.

Season with salt and pepper to taste, then chill in the refrigerator for at least 30 minutes.