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Preheat oven to 425°F.
Toss squash and 1 tablespoon oil in a large bowl. Spread out on a large rimmed baking sheet. Roast for 10 minutes.
Meanwhile, toss broccoli, bell peppers, onion, Italian seasoning (or herbes de Provence), salt and pepper in the bowl with the remaining 2 tablespoons olive oil until the vegetables are evenly coated.
Add the squash to the vegetables in the bowl. Toss to combine. Spread the vegetables out on 2 large rimmed baking sheets, dividing evenly. Roast, stirring once or twice, until the vegetables are tender and browned in spots, 17 to 20 minutes. Drizzle with vinegar.