San Francisco, From $108 a Night
This festive hotel package is valid over the holidays and includes ice-skating at Union Square.
How will you protect my money? Most have an escrow account to ensure they aren't using your money to fund someone else's trip. Ask for the name of the bank and a letter stating you'll get reimbursed if the operator goes belly up.
What's your cancellation policy? Make sure they have one—then scrutinize the terms.
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Do you have general liability insurance? This coverage demonstrates solvency. Legitimate agencies should have it.
Can you give me references? Ask past clients and travel agents to tell you what it's like doing business with the operator.
Plus: Read these 40 Best Deals guidelines before booking any package.