Family and group travel — group stays

Is family and group travel the right trip for your group?

This is for multigenerational families and friend groups who want one roof rather than several hotel rooms. The Sunkiss and The Scottsdale Social suit pool-centred Arizona trips; The Evergreen and The Tamarack suit Montana trips built around the outdoors. Any season works, with Arizona best in the cooler months and Montana strongest in summer and fall. One practical constraint: the permitted overnight occupancy governs, not the number of beds. Compare the four homes side by side before you invite the full list.

Compare all four homes side by side

Last reviewed 2026-09-20

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.

Matching the house to the family

In Scottsdale, The Sunkiss sleeps up to 16 with four king bedrooms and a bunk room, and The Scottsdale Social sleeps up to 18 with three king bedrooms, a two-queen room and a bunk room. Both have a private pool; The Scottsdale Social offers a removable pool safety fence that can be installed before arrival if you ask.

In Montana, The Evergreen sleeps up to 10 with a bunk room of two twin-over-twin bunks, and The Tamarack sleeps up to 10 with two bunk rooms, a kids' playroom and a climbing wall for bad-weather days.

Room plans for three generations

Put grandparents in the room closest to a bathroom and away from the main gathering space. Give each family with young children a room near the bunk room, so older kids can share while parents stay close. Teenagers usually prefer the bunk room to a room with their parents. Write the plan down before arrival so nobody negotiates at midnight.

A family day that works

Build around naps, meals and one main outing:

Morning: the main outing while energy is high — a lake beach in Montana, an early hike or pool time in Arizona.
Midday: back at the house for lunch and rest.
Afternoon: games, the playroom or the pool, with adults taking turns on supervision.
Evening: one big meal at home, then hot tub for the adults.

Seasons for family trips

School holidays fill first in both destinations. Scottsdale's cooler months suit outdoor time with children; summer means early mornings and the pool. In the Flathead Valley, summer is lake season, while fall and winter trips lean on the houses' indoor space and hot tubs.

Related planning

Questions groups ask

Which Trailstead home is best for young children?

It depends on the destination. The Tamarack has a kids' playroom and climbing wall; The Scottsdale Social offers a removable pool safety fence on request. Check each home's own site for full details.

Is the bed count the same as the guest limit?

No. The maximum overnight occupancy governs, not the number of beds. Each home's limit is shown on its page and booking calendar.

Can two families book two homes for one trip?

Yes, in the same destination, as two separate stays. Each home has its own reservation, guest limit and house rules.

Watch

See the trip

Kids playroom and climbing wall at The Tamarack | Lakeside, Montana

Every family trip needs an indoor backup plan, and at The Tamarack it is the kids' playroom and climbing wall. When Montana weather turns, or younger guests need a break from the lake and the trails, the playroom keeps them busy at the house while the adults stay close by. The rest of the home suits the same kind of trip: a game room, a hot tub and sauna, and six bedrooms including two bunk rooms that work well for children. The Tamarack sleeps up to 10 guests, with a maximum of 10 overnight. Build the valley itinerary first, then check that the house fits it on The Tamarack's official booking page.

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Stays

Homes that suit this trip

Somers, Montana

The Evergreen at Flathead Lake

Room to reconnect. Montana to explore.

6 bedrooms · 10 beds · 3.5 baths · 4.98 (42) · checked 23 Sep 2026

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, near Flathead Lake and Glacier Country.

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

Sleeps up to 10. Six bedrooms, ten beds and 3.5 bathrooms. Maximum 10 guests overnight per local regulations.

View detailsSee dates and your full stay totalBook direct on our Guesty booking portal.

Scottsdale, Arizona

The Sunkiss Scottsdale

Serve. Swim. Stay awhile.

5 bedrooms · 8 beds · 3 baths · 4.93 (60) · checked 23 Sep 2026

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 up to 16. Five bedrooms, eight beds and three bathrooms. Maximum 16 guests overnight.

View detailsSee dates and your full stay totalBook direct on our Guesty booking portal.

Lakeside, Montana

The Tamarack

Adventure out. Exhale in.

6 bedrooms · 9 beds plus trundle · 4.5 baths · 5.0 (12) · checked 23 Sep 2026

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

Sleeps up to 10. Six bedrooms, nine beds plus trundle and 4.5 bathrooms. Maximum 10 guests overnight.

View detailsSee dates and your full stay totalBook direct on our Guesty booking portal.

Keep planning

Flathead Valley events and seasonal planning
Which weeks fill first, with links to the official calendars.
Scottsdale events and seasonal planning
Which weeks fill first, with links to the official calendars.
Planning a stay in Flathead Valley
Season by season, and what the area gives a group.
Planning a stay in Scottsdale
Season by season, and what the area gives a group.
Every kind of trip we plan for
Back to the full list of trip types.
Compare all four homes
Sleeping arrangements and official booking calendars.