The Tilly Jane Guard Station is ONLY available weekends during the winter months. This is primarily due to firewood usage and storage capacity limits, thus it books up quickly. Check the Reserve America website occasionally as cancellations do occur. You may be able to pick one up if your lucky.
There is a second “cabin” in the Tilly Jane area, the Tilly Jane A-Frame is located across Tilly Jane Creek from the Tilly Jane Guard Station (used only on weekends), and is open for year around reservations at Reserve America, pretty much every day of the week. The A-Frame (or TJAF) is a shared shelter that takes reservations up to a maximum of 20 people per night at $15 per night per person. During peak season (~January thru mid-March) the A-Frame slots fill up on weekends, especially Saturday nights, but mid-week nights are much more available.
The A-Frame is a rustic “primitive” shelter with a large woodstove and covered wood supply, and some other basics like propane camp lanterns (bring your own 16-oz canister). Bring your own stove and cooking stuff and all, just like backpacking. Boil creek water or melt snow for water not packed in. Contact the folks that manage that shelter at: firstname.lastname@example.org.
The Tilly Jane A-Frame is managed by the Portland Chapter of the Oregon Nordic Club (ONC) under a permit with the US Forest Service. Joining the ONC-Portland Chapter allows free use as a member (or volunteer) of the ONC’s weekends at the TJAF. Contact the same gmail account above for questions, but the free weekends are every month in peak season and tend to be lightly used. The classic log structure was built by the CCC in 1939 and is the newest building in the Cloud Cap – Tilly Jane Historic District,
The nearby Tilly Jane Guard Station (or TJGS) is much smaller (8 people is “full”), and has been difficult to reserve over the past 30-years or so due to its popularity. Propane lighting and cooking and a big fireplace make it a cozy little winter shelter, but it gets reserved (~$225/weekend) within minutes of availability on www.reserveamerica.com; sorry. It has been managed by the Columbia Gorge Chapter of the ONC since the mid-1980s.
Winter access to the Tilly Jane and Cloud Cap areas is via the Tilly Jane Ski Trail (FS Trail #643) and is a pretty tough hike/ climb or snowshoe trip up: 1,900-ft elevation gain over less than 3.0-miles, so a lot of “efficient ascending”. Snowshoes or climbing skins on your skis are highly recommended. The trailhead is at a Sno-Park (elev. 3,800-ft) below the Cooper Spur ski area; Tilly Jane area is at 5,700-ft elevation and has best snow conditions; another mile or so above the cabins and you are above tree line, so it is high on Mount Hood. Descending the same trail is okay on snowshoes but require at least intermediate downhill skills on skis; ask about alternate routes like the Cloud Cap Road (9-miles) if concerned about the descent.