Come wintertime, there’s nothing quite like escaping to a cozy cabin or mountainside retreat where the whole family can unwind, reconnect, and make lasting memories. Whether you’re looking to spend Christmas morning by a crackling fire, sled in freshly fallen snow, or soak in a hot tub beneath starry skies, these winter-ready Airbnbs offer everything from alpine adventures to quiet woodland seclusion—all thoughtfully tailored for family friendly winter vacations.
With holiday planning underway, we’ve curated a collection of homes across North America—from the towering peaks of Colorado and Montana to the nostalgic forests of New England and the storybook charm of Quebéc—that fit this criteria. Each listing is chosen not just for its style and setting, but for its family-first amenities: travel cribs, bunk beds, board games, sledding hills, and room to gather. These homes are places where you can cook a holiday meal together, cozy up for movie night, or simply watch the snow fall in peace (and modern comforts). Whether you’re planning for a white Christmas or a midwinter escape, these 13 stays bring the magic of the season to life—with plenty of space for the people who matter most.
Note: Many of these homes are tucked deep in nature or perched along winding, snow-covered roads—part of their charm, but also something to plan for. Several require four-wheel drive or snow tires in the winter months. Be sure to coordinate with hosts in advance; most are happy to offer guidance on road conditions, parking, and the best way to safely reach the property, whether that be mandatory four-wheel-drive rentals or professional shuttle services.
We’ve vetted these listings based on Superhost or Guest Favorite status, ratings, amenities, location, previous guest reviews, and decor.
