Experience

Family and group travel

One roof, several generations, and a plan that survives contact with a real family.

Multigenerational trips fail on logistics more often than on scenery. The useful questions are where people sleep, where they gather, how many bathrooms there are, and how far the nearest grocery run is.

Every Trailstead home publishes its sleeping arrangements and guest limits on its own booking page. Check those limits before you invite the full list — the maximum overnight occupancy is what governs, not the number of beds.

Stays

Homes that suit this trip

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. Montana rules govern how overnight occupancy is advertised, so we publish a maximum of ten — the same number shown on the home's own site. Travelling with more? Ask on the booking page before you book.

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Scottsdale, Arizona

The Sunkiss

Serve. Swim. Stay awhile.

5 bedrooms · beds · 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

Sleeps 16+. Final guest limits are confirmed on the official booking page.

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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

Sleeps up to 18. Final guest limits are confirmed on the official booking page.

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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. Montana rules govern how overnight occupancy is advertised, so we publish a maximum of ten — the same number shown on the home's own site. Travelling with more? Ask on the booking page before you book.

Tour this home Check availability