If you like the idea of backpacking to a beautiful, remote place to spend the night, but you don’t love the notion of sleeping on the ground, let us introduce you to West Point Inn (from $100), a rustic backcountry hotel with seven rooms and six cabins on a ridge atop California’s Mount Tamalpais, less than an hour north of San Francisco. To get to the inn, you’ll hike or bike two miles from Mount Tamalpais State Park, near the town of Mill Valley, on a path once used by a historic scenic railway. It’s just far enough to feel like you’ve earned a good night’s sleep, but not so far that you can’t bring the kids. The hotel, which was built in 1904 as a restaurant and pitstop for the railroad, has the charm of a backcountry hut but a few more amenities—think plush quilts and running water. You’ll still need to bring your own sheets and food and share a bathroom down the hall. But from the main porch you can enjoy unparalleled views of the Marin Headlands and the East Bay, as well as occasional sightings of the Golden Gate Bridge through the fog. In the winter, temperatures are still comfortable for daytime hiking and inn availability is much easier to snag. —Megan Michelson