Skip to content
Trailstead Stays
Explore stays

Experience

Reunions, graduations and celebrations

Weddings, graduations, family visits and the reunions that only happen once a decade.

Milestone trips are about the house being the venue for the group's own time rather than a base for going out. That makes gathering space, bathrooms and the published guest limit the three things worth settling before invitations go out.

These are guest homes in residential neighbourhoods, not event venues. Confirm the guest limit and any gathering rules on the home's own booking page before you plan anything around a headcount — and in Montana, overnight bookings remain capped at a maximum overnight occupancy of 10.

For a party too large for one house, the two Scottsdale homes can be taken together and the group still gathers in a single backyard. Each is reserved on its own booking calendar.

Stays

Homes that suit this trip

Scottsdale, Arizona

The Scottsdale Social

Made to play. Built to gather.

5 bedrooms · 9 beds · 3 baths · 4.91 (68)

The larger of the two Scottsdale houses, built around shared time. Five bedrooms and nine beds, a private backyard with pool, hot tub and putting green, and more than fifteen games for the evenings nobody wants to go out.

  • Group celebrations and reunions
  • Golf trips
  • Holiday gatherings

Five bedrooms and nine beds, with sleeping arrangements for up to 18. Final guest limits are confirmed on the booking calendar.

Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

Scottsdale, Arizona

The Sunkiss

Serve. Swim. Stay awhile.

5 bedrooms · 3 baths · 4.93 (58)

A Scottsdale home shaped around outdoor time. Four king bedrooms and a bunk room, a private pool and hot tub, and a sport court set up for pickleball and basketball. It suits groups who want to play during the day and stay in for a long evening together.

  • Golf and pickleball groups
  • Family and multigenerational trips
  • Cooler-season desert escapes

Five bedrooms with sleeping arrangements for 16+. Final guest limits are confirmed on the booking calendar.

Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

Somers, Montana

The Evergreen

Room to reconnect. Montana to explore.

6 bedrooms · 10 beds · 3.5 baths · 4.97 (39)

A six-bedroom Montana home for groups that want one roof instead of several. A private hot tub and barrel sauna outside, a speakeasy and game room inside, and Flathead Lake a short drive away with Glacier Country under an hour on.

  • Multigenerational family trips
  • Flathead Lake and Glacier planning
  • Fall and winter gatherings

Six bedrooms and ten beds, with sleeping arrangements for 18–20 guests. Overnight bookings remain capped at a maximum overnight occupancy of 10, as advertised under Montana rules.

Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

Lakeside, Montana

The Tamarack

Adventure out. Exhale in.

6 bedrooms · 9 beds · 4.5 baths · 5.0 (12)

A six-bedroom Montana lodge for groups that plan to be outside most of the day. Hot tub, sauna, fire pit and game room, room for gear and vehicles, and a setting built for golden-larch fall drives and winter ski days.

  • Lake trips
  • Group retreats
  • Ski and winter weekends

Six bedrooms and nine beds, with sleeping arrangements for up to 16 guests. Overnight bookings remain capped at a maximum overnight occupancy of 10, as advertised under Montana rules.

Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)