Where do I report the sale of a vacation home that I’ve owned for years?

A vacation home is a capital asset. As such, gain is reported on Schedule D (after entering the transaction on Form 8949 in the space for long-term transactions not reported on Form 1099-B). If the sale resulted in a loss, you may not deduct it because a loss on the sale of personal-use property is not deductible. You do not have to report the loss transaction on Form 8949 or Schedule D unless you received a Form 1099-S for it; in that case, you must enter an adjustment on Form 8949/Schedule D to indicate the loss is not deductible.